天堂网亚洲,天天操天天搞,91视频高清,菠萝蜜视频在线观看入口,美女视频性感美女视频,95丝袜美女视频国产,超高清美女视频图片

Home Cart 0 Sign in  

[ CAS No. 5750-76-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 5750-76-5
Chemical Structure| 5750-76-5
Structure of 5750-76-5 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 5750-76-5 ]

Related Doc. of [ 5750-76-5 ]

Alternatived Products of [ 5750-76-5 ]
Product Citations

Product Details of [ 5750-76-5 ]

CAS No. :5750-76-5 MDL No. :MFCD03788200
Formula : C4HCl3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :GIKMWFAAEIACRF-UHFFFAOYSA-N
M.W : 183.42 Pubchem ID :237259
Synonyms :

Calculated chemistry of [ 5750-76-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.06
TPSA : 25.78 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 2.75
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 1.43
Log Po/w (SILICOS-IT) : 2.99
Consensus Log Po/w : 2.3

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.2
Solubility : 0.115 mg/ml ; 0.000627 mol/l
Class : Soluble
Log S (Ali) : -2.95
Solubility : 0.208 mg/ml ; 0.00113 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.5
Solubility : 0.0579 mg/ml ; 0.000316 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 5750-76-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5750-76-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 5750-76-5 ]

[ 5750-76-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 5750-76-5 ]
  • [ 50919-07-8 ]
  • [ 1236130-84-9 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate; In N,N-dimethyl-formamide; Step A: 2,5-Dichloro-N-[(1S)-1-(3-methoxyphenyl)ethyl]pyrimidin-4-amine To a solution of (1S)-1-(3-methoxyphenyl)ethanamine (1.50 g, 9.92 mol) (S-isomer, >99% ee purity) and 2,4,5-trichloropyrimidine (1.19 mL, 10.4 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.1 g, 30 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. Then EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and then dried (Na2SO4), filtered, and concentrated to give the desired product as a light yellow thick oil (2.84 g, 96%). LCMS for C13H14Cl2N3O (M+H)+: m/z=298.0, 300.0, 302.0 (9:6:1).
  • 2
  • [ 887581-09-1 ]
  • [ 5750-76-5 ]
  • [ 1236130-92-9 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; Step B: N-(2-Bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amine To a solution of 1-<strong>[887581-09-1](2-bromo-5-methoxyphenyl)methanamine</strong> (3.6 g, 13 mmol) and 2,4,5-trichloropyrimidine (1.60 mL, 14 mmol) in N,N-dimethylformamide (41.3 mL) was added potassium carbonate (5.53 g, 40 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated to give the desired product as a light yellow gel (4.65 g, 96%). LCMS for C12H10BrCl2N3O (M+H)+: m/z=361.9, 363.9.
  • 3
  • [ 842136-58-7 ]
  • [ 5750-76-5 ]
  • [ 1263374-62-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 80℃; Step 1. Preparation of 2,5-dichloro-4-(6-fluoropyridin-2-yl)pyrimidine; A mixture of 2,4,5-trichloropyrimidine (49.3 mg, 0.269 mmol), <strong>[842136-58-7]2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine</strong> (50 mg, 0.224 mmol), PdCl2(dppf).CH2Cl2 adduct (18.31 mg, 0.022 mmol), DME (0.7 ml), and 2M sodium carbonate (0.247 ml, 0.493 mmol) reaction mixture was stirred at about 80 C. until the reaction mixture was complete, as indicated by LCMS. The reaction mixture mixture was cooled, diluted with 5 ml of ethyl acetate and 1 ml of methanol, filtered and concentrated to yield a crude solid. The crude material was purified by silica gel chromatography using a 12 g column, eluting from 0%-40% ethyl acetate with hexane. The desired fractions were concentrated to constant mass, to yield 39.5 mg of titled compound as a free base. LCMS (m/z): 244.0 (MH+), retention time=0.89 min.
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; ethanol; at 80℃; A mixture of 2,4,5-trichloropyrimidine (49.3 mg, 0.269 mmol), 2-fluoro-6-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (50 mg, 0.224 mmol), PdCl2(dppf).CH2Cl2 adduct (18.31 mg, 0.022 mmol), DME (0.7 ml), and 2M sodium carbonate (0.247 ml, 0.493 mmol) reaction mixture was stirred at about 80 C until the reaction mixture was complete, as indicated by LCMS. The reaction mixture was cooled, diluted with 5 ml of ethyl acetate and 1 ml of methanol, filtered and concentrated to yield a crude solid. The crude material was purified by silica gel chromatography using a 12g column, eluting from 0%-40% ethyl acetate with hexane. The desired fractions were concentrated to constant mass, to yield 39.5 mg of titled compound as a free base. LCMS (m/z): 244.0 (MH+), retention time = 0.89 min
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 80℃; Example 3 (Compound 3)frans-N1-(5-chloro-4-(6-(cyclohexylmethylamino)pyridin-2-yl)pyrimidin-2-yl)cyclohexane- 1 ,4-diamine Step 1. Preparation of 2,5-dichloro-4-(6-fluoropyridin-2-yl)pyrimidine A mixture of 2,4,5-trichloropyrimidine (49.3 mg, 0.269 mmol), 2-fluoro-6-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (50 mg, 0.224 mmol), PdCl2(dppf).CH2Cl2 adduct (18.31 mg, 0.022 mmol), DME (0.7 ml), and 2M sodium carbonate (0.247 ml, 0.493 mmol) reaction mixture was stirred at about 80 C until the reaction mixture was complete, as indicated by LCMS. The reaction mixture was cooled, diluted with 5 ml of ethyl acetate and 1 ml of methanol, filtered and concentrated to yield a crude solid. The crude material was purified by silica gel chromatography using a 12g column, eluting from 0%-40% ethyl acetate with hexane. The desired fractions were concentrated to constant mass, to yield 39.5 mg of titled compound as a free base. LCMS (m/z): 244.0 (MH+), retention time = 0.89 min.
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 80℃; Example 3 (Compound 3)frans-N1-(5-chloro-4-(6-(cyclohexylmethylamino)pyridin-2-yl)pyrimidin-2-yl)cyclohexane- 1 ,4-diamine Step 1. Preparation of 2,5-dichloro-4-(6-fluoropyridin-2-yl)pyrimidine A mixture of 2,4,5-trichloropyrimidine (49.3 mg, 0.269 mmol), 2-fluoro-6-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (50 mg, 0.224 mmol), PdCl2(dppf).CH2Cl2 adduct (18.31 mg, 0.022 mmol), DME (0.7 ml), and 2M sodium carbonate (0.247 ml, 0.493 mmol) reaction mixture was stirred at about 80 C until the reaction mixture was complete, as indicated by LCMS. The reaction mixture was cooled, diluted with 5 ml of ethyl acetate and 1 ml of methanol, filtered and concentrated to yield a crude solid. The crude material was purified by silica gel chromatography using a 12g column, eluting from 0%-40% ethyl acetate with hexane. The desired fractions were concentrated to constant mass, to yield 39.5 mg of titled compound as a free base. LCMS (m/z): 244.0 (MH+), retention time = 0.89 min.
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 80℃; A mixture of 2,4,5-trichloropyrimidine (49.3 mg, 0.269 mmol), 2-fluoro-6-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (50 mg, 0.224 mmol), PdCI2(dppf).CH2Cl2 adduct (18.31 mg, 0.022 mmol), DME (0.7 ml), and 2M sodium carbonate (0.247 ml, 0.493 mmol) reaction mixture was stirred at about 80 C until the reaction mixture was complete, as indicated by LCMS. The reaction mixture was cooled, diluted with 5 ml of ethyl acetate and 1 ml of methanol, filtered and concentrated to yield a crude solid. The crude material was purified by silica gel chromatography using a 12g column, eluting from 0%-40% ethyl acetate with hexane. The desired fractions were concentrated to constant mass, to yield 39.5 mg of titled compound as a free base. LCMS (m/z): 244.0 (MH+), retention time = 0.89 min.

  • 4
  • [ 6358-77-6 ]
  • [ 5750-76-5 ]
  • [ 1352244-16-6 ]
  • 5
  • [ 1197953-47-1 ]
  • [ 5750-76-5 ]
  • [ 1197953-49-3 ]
YieldReaction ConditionsOperation in experiment
84.6% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 4.0h; 25 mL of a one-necked flask was added DMF (3 mL),2,5,6-trichloropyrimidine (0.72 g, 3.9 mmol) was added successively with stirring,2- (dimethylphosphonino) aniline (0.5 g, 3 mmol)Anhydrous potassium carbonate (0.62 g, 4.5 mmol), heated to 60 ° C and stirred for 4 h.(30 mL x 2), the organic phase was combined, washed with water (60 mL x 2), and the organic layer was dried over anhydrous sodium sulfate, and the organic layer was washed with ethyl acetate (30 mL) and water (30 mL) Filtered and concentrated, and the residue was passed through a silica gel column to give 0.8 g of a pale yellow solid in 84.6percent yield.
69% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 5.0h; (2-aminophenyl)dimethyl phosphorus oxide (8.76 g, 51.81 mmol), 2,4,5-trichloropyrimidine (14.92 g, 81.35 mmol), anhydrouspotassium carbonate (22.49 g, 162.29 mmol) and N,N-dimethylformamide (50 mL) were added in a 100 mLsingle-necked flask, and the mixture was heated to 60°C and reacted for 5 hours. After the reaction was completed, thereaction solution was cooled down to room temperature, added with water (30mL) and extracted with dichloromethane(100 mL 3 3), washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered by suction, andevaporated under reduced pressure to remove the solvent. The resulting crude product was subjected to silica gelcolumn chromatography (mobile phase, dichloromethane : methanol = 40 : 1) to give (2-((2,5-dichloropyrimidin-4-yl)amino)phenyl)dimethyl phosphorus oxide (11.3 g, 69.0percent yield).1H-NMR (300 MHz, CDCl3) : delta = 11.55 (s, 2H), 8.67 (dd, J = 4.4, 8.5 Hz, 1H), 8.22 (s, 1H), 7.59 (dd, J = 7.7, 8.1 Hz,1H), 1.86 (s, 3H), 1.82 (s, 3H). 13C-NMR (75 MHz, CDCl3) : delta = 156.85, 155.10, 133.05, 133.03, 129.77, 129.63, 123.56,123.40, 122.18, 122.09, 19.28, 18.33.HRMS (ESI, [M+H]+) m/z: 316.0175.
68.4% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 16 - 70℃; for 16.0h; At 16 deg.C , Example 1K (2.50 g, 14.8 mmol) and 2,4,5-trichloropyrimidine (2.85 g, 15.5 mmol) in DMF (20mL) mixture was added DIPEA (3.82 g, 29.6 mmol). The reaction mixture was heated to 70 deg. C and stirred for 16 hours. TLC showed the reaction was complete. The reaction mixture was washed with water (50 mL) diluted (40mL × 3) and extracted with EtOAc. The combined organic phases were washed with saturated brine (20mL × 2), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was recrystallized from ethanol to give the title compound (3.20 g, 10.1 mmol, 68.4percent yield) as a white solid.
61% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 5.0h; Step 2: Synthesis of 2:2,4,5-Trichloropyrimidine (1.57 eq), 1 (1.0 eq), and potassium carbonate (3.14 eq) in DMF were stirred at 60 °C for 5 hours and then cooled to room temperature. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (ISCO machine) (DCM/MeOH 20: 1 ) to give 2 as a yellow solid (61 percent yield).
61% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 5.0h; 2,4,5-Trichloropyrimidine (1.57 eq), 1 (1.0 eq), and potassium carbonate (3.14 eq) in DMF were stirred at 60 °C for 5 hours and then cooled to room temperature. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (ISCO machine) (DCM/MeOH 20:1) to give 2 as a yellow solid (61 percent yield).
50% With N-ethyl-N,N-diisopropylamine; for 12.0h;Reflux; A solution of 2,4,5-trichloropyrimidine(1.82 g, 10 mmol), (2-aminophenyl)dimethylphosphine oxide(1.69 g, 10 mmol) and N,N-diisopropylethylamine (1.94 g, 15 mmol)in propan-2-ol (25 mL) was heated under reflux for 12 h. The solvent was removed by evaporation and the residue was dissolvedin CH2Cl2 (100 mL). The solution was washed with water andsaturated sodium chloride solution and dried, filtered andconcentrated. The residuewas purified by flash chromatography onsilica gel (0e2percent MeOH in DCM) to afford compound 51l (1.60 g,50percent). 1H NMR (400 MHz, DMSO-d6) delta 11.84 (s, 1H), 8.43 (s, 2H), 7.62(s, 2H), 7.25 (s, 1H), 1.83 (s, 3H), 1.80 (s, 3H); 13C NMR (100 MHz,DMSO-d6) d 157.01, 155.99, 142.48, 132.73, 131.47 (d, J 10 Hz),124.17 (d, J 6.0 Hz), 122.64, 122.06 (d, J 3.0 Hz), 121.73, 115.30,18.98, 18.28. HRMS (ESI, m/z) [M+H]+ calcd for C12H13Cl2N3OP:316.0173, found: 316.0175.
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In N,N-dimethyl-formamide; at 65℃; [00369] 245-trichloropyrimidine (54.2 g, 0296 mol, 1.0 eq.), (2arninophenyl)dimethyl..phosphine oxide (50.Og, 0.296 mole, 1.0 eq.), potassium carbonate (49.lg, 0355 mol, 1.2 eq.) and tetrabutylammonium bisuifate (10.2 g. 0.03 mole, 0.1 eq.) were combined in DMF (1050 mL), and heated at 65° C for -8.0-8.5 h. During the course of heating, an offwhite suspension formed. Upon coong, the mixture was cooled to rt and filtered. The coHected solids were rinsed with DMF (2 x 50 mL), and the combined filtrates were concentrated in vacuo. The resulting residue was dissolved in EtOAc (1 .3 L) and water (350 mL). The aqueous layer was isolated and extracted with EtOAc (2 x 250 mL). The combined organic layers were washed with brine (20percent w/w, 500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford (2..((25dichloropyriniidin4 yl)amino)phenyl)dimethylphosphine oxide as an offwhite solid.
With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; General procedure: To a solution of 2,4-dichloro-5-fluoropyrimidine (0.5 g, 2.99 mmol) and (2-aminophenyl)dimethylphosphineoxide (0.323 g, 1.907 mmol) in DMF (6.36 mL) wasadded potassium carbonate (0.828 g, 5.99 mmol). The reactionmixture was stirred at 70 °C for overnight. After completion of thereaction, the resulting mixture was cooled to room temperature,quenched with water, extracted with DCM and washed with brine.The combined organic layer was dried over Na2SO4, filtered andconcentrated under reduced pressure. The residue was purified byflash column chromatography on silica gel (0-20percent MeOH in DCM)to give 3f as a yellowish solid (0.178 g, 31percent).
17 g at 75℃; for 6.0h; 2-iodoaniline (17.5 g, 79.9 mmol) and dimethyl phosphine oxide (6.9 g, 88.5 mmol) were added,Palladium acetate (0.3 g, 1.3 mmol), Xantphos (0.77 g, 1.3 mmol),N,N-diisopropylethylamine (22.7 g, 175.8 mmol), DMF (50 mL),Magnetic stirring. Under nitrogen protection, heat to 100°C for 6 hours,The 2-iodoaniline consumption was monitored by thin layer chromatography. Cool to room temperature2,4,5-trichloropyrimidine (17.5 g, 95.9 mmol) was added and the reaction was heated to 75°C for 6 hours.The reaction was complete by thin layer chromatography. Cool to room temperature, add water 300mL,Adjust pH to 5 with 5percent hydrochloric acid and extract with ethyl acetate (100 mL x 3).Wash with sodium bicarbonate solution (100 mL), wash with saturated sodium chloride solution (100 mL × 2),Dry over anhydrous sodium sulfate. It is filtered with suction and concentrated to give a crude brown solid.Recrystallization with ethyl acetate/petroleum ether (volume ratio 1:2) gave an almost white solid 17g.Yield 67.3percent.
0.7 g With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; Compound b1-1 (0.5 g, 3 mmol) was placed in a 100 mL three-necked flask, and DMF (30 mL) was added.Then, compound b2 (0.86 g, 4.7 mmol), anhydrous potassium carbonate (1.23 g, 9.5 mmol) was added, and stirred at 60 ° C overnight.TLC showed the reaction was almost complete, cooled to room temperature, and then water (100 mL)The organic phase was washed with brine and dried over anhydrous magnesium sulfate.Concentrated through the column to give 0.7 g of a yellow solid.

  • 6
  • [ 5369-19-7 ]
  • [ 5750-76-5 ]
  • 2,5-dichloro-N<SUP>4</SUP>-(3-tert-butylphenyl)pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With N-ethyl-N,N-diisopropylamine; In ethanol; for 14h;Reflux; 2,5-Dichloro-iV4-(3-teri-butylphenyl)pyrimidin-4-amine (SG1-175): A solution of 2,4,5-trichloropyrimidine (1.00 g), 3-(tert-butyl)aniline (0.813 mg), and DIPEA (5.70 mL) in EtOH (5 mL) was heated at reflux for 14 h. The mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and washed with water (2 x 50 mL) and brine (50 mL). The organic layer was dried (Na2S04) and concentrated under reduced pressure to give the title compound as a brown solid (1.545 g, 96percent). Mp: 107-110 °C. NMR (400 MHz, DMSO-i): delta 9.48 (s, 1H, disappeared on D2O shake), 8.35 (s, 1H), 7.62 (t, J= 1.9 Hz, 1H), 7.41 (ddd, J= 7.8, 1.9, 1.0 Hz, 1H), 7.29 (t, J = 7.8 Hz, 1H), 7.19 (ddd, J= 7.8, 1.9, 1.0 Hz, 1H), 1.27 (s, 9H). HPLC-MS (ESI+): m/z 300.1 [10percent, (M37C137C1+H)+], 298.1 [65percent, (M35C137C1+H)+], 296.1 [100percent, (M35C135C1+H)+].
96% With N-ethyl-N,N-diisopropylamine; In ethanol; for 14h;Reflux; A solution of 2,4,5-trichloropyrimidine (1.00 g), 3-(i<?ri-butyl)aniline (0.813 mg), and DIPEA (5.70 mL) in EtOH (5 mL) was heated at reflux for 14 h. The mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and washed with water (2 x 50 mL) and brine (50 mL). The organic layer was dried (Na2S04) and concentrated under reduced pressure to give the title compound as a brown solid (1.545 g, 96percent). Mp: 107-110 °C. NMR (400 MHz, DMSO-ifc): delta 9.48 (s, IH, disappeared on D20 shake), 8.35 (s, IH), 7.62 (t, / = 1.9 Hz, IH), 7.41 (ddd, J = 7.8, 1.9, 1.0 Hz, IH), 7.29 (t, / = 7.8 Hz, IH), 7.19 (ddd, / = 7.8, 1.9, 1.0 Hz, IH), 1.27 (s, 9H). HPLC-MS (ESI+): m/z 300.1 [10percent, (M37C137C1+H)+], 298.1 [65percent, (M35C137C1+H)+], 296.1 [100percent, (M35C135C1+H)+].
  • 7
  • [ 20876-36-2 ]
  • [ 5750-76-5 ]
  • 5-((2,5-cichloropyrimidin-4-yl)amino)indolin-2-one [ No CAS ]
  • 8
  • (2-aminophenyl)dimethylphosphine oxide hydrochloride [ No CAS ]
  • [ 5750-76-5 ]
  • [ 1197953-49-3 ]
YieldReaction ConditionsOperation in experiment
79% With N-ethyl-N,N-diisopropylamine; In ethanol; at 80℃; for 18h;Large scale; o a solution of (2-aminophenyl) dimethylphosphine oxide hydrochloride (900 g, 4.16 mil) in ethanol (600 mL) was addedDIPEA (1.24 Kg, 1.67 L, 9.56 mil, 2.3 eq)It was observed that the solution became clear,Then 2,4,5-trichloropyrimidine was added(915.238,4.99 11,1,1 equivalent)The The reaction mixture was heated to 80 (and stirred for 18 hours.The reaction was complete and the reaction mixture was concentrated by cooling the reaction solution.Water (2 L) and DCM (2 L) were added and stirred for 0.5 h. After separation, the aqueous phase was extracted with DCM (500 mL x 3) and the combined organic phases were washed with saturated brine (2 L), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. After concentration to give a brown solid, the crude product was washed with methyl tert-butyl ether beating and filtered to give the title compound as a white solid (l.KKK, yield 79%)
79% With N-ethyl-N,N-diisopropylamine; In ethanol; at 80℃; for 18h;Large scale; To a solution of (2-aminophenyl) dimethylphosphine oxide hydrochloride (900 g, 4.16 mol) in ethanol (600 mL) was added DIPEA (1.24 Kg, 1.67 L, 9.56 mol, 2.3 equivalents), and the solution became clear. Then 2,4,5-trichloropyrimidine (915.23 g, 4.99 mol, 1.2 equivalents) was added.The reaction mixture was heated to 80 C and stirred for 18 hours. TLC (EtOAc) showed the reaction was complete. After the reaction solution was cooled, the reaction mixture was concentrated, water (2L) and DCM (2L) were added and stirred for 0.5 hours. After separation, the aqueous phase was added to DCM (500 mL x 3) and extracted. The combined organic phases were washed with saturated brine (2 L), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. After concentration, a brown solid was obtained. The crude product was washed with methyl tert-butyl ether and filtered to obtain the target compound as a white solid (1.04 Kg, yield 79%).
  • 9
  • [ 5750-76-5 ]
  • [ 57631-05-7 ]
  • 1-(2-chloropyrimidin-4-yl)-3-trifluoromethyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
A solution of 3-triflouromethylindazole (931 mg, 5.0 mmol) in dry DMF (15 mL) cooled to 0 C is treated with NaH (200 mg, 5.0 mmol, 60% in mineral oil). After stirring at 25 C for 2 h the mixture is cooled to 0 C and 2,4,5-dichloropyrimidine (745 mg, 5.0 mmol) is added. After stirring for 4 h the mixture is quenched with water (50 mL) and extracted with ethyl acetate (3 x 25 mL), washed with water (2 x 25 mL) and saturated brine (25 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (Pet/EtOAc 20/1) to afford 1-(2-chloropyrimidin-4-yl)-<strong>[57631-05-7]3-trifluoromethyl-1H-indazole</strong> as a white solid.
  • 10
  • [ 5750-76-5 ]
  • [ 57631-05-7 ]
  • 1-(2,5-dichloropyrimidin-4-yl)-3-trifluoromethyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
A solution of 3-triflouromethylindazole (931 mg, 5.0 mmol) in dry DMF (15 mL) cooled to 0 C is treated with NaH (200 mg, 5.0 mmol, 60% in mineral oil). After stirring at 25 C for 2 h the mixture is cooled to 0 C and 2,4,5-trichloropyrimidine (917 mg, 5.0 mmol) is added. After stirring for 4 h the mixture is quenched with water (50 mL) and extracted with ethyl acetate (3 x 25 mL), washed with water (2 x 25 mL) and saturated brine (25 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (Pet/EtOAc 20/1) to afford 1-(2,5-dichloropyrimidin-4- yl)-<strong>[57631-05-7]3-trifluoromethyl-1H-indazole</strong> as a white solid.
  • 11
  • [ 2026-70-2 ]
  • [ 5750-76-5 ]
  • 2,5-dichloro-N-methyl-N-(3-(trifluoromethyl)phenyl)pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With N-ethyl-N,N-diisopropylamine; for 12h;Reflux; General procedure: A solution of 2,4,5-trichloropyrimidine(1.82 g, 10 mmol), (2-aminophenyl)dimethylphosphine oxide(1.69 g, 10 mmol) and N,N-diisopropylethylamine (1.94 g, 15 mmol)in propan-2-ol (25 mL) was heated under reflux for 12 h. The solvent was removed by evaporation and the residue was dissolvedin CH2Cl2 (100 mL). The solution was washed with water andsaturated sodium chloride solution and dried, filtered andconcentrated. The residuewas purified by flash chromatography onsilica gel (0e2% MeOH in DCM) to afford compound 51l (1.60 g,50%).
Recommend Products
Same Skeleton Products

Technical Information

Historical Records

Related Functional Groups of
[ 5750-76-5 ]

Chlorides

Chemical Structure| 1780-40-1

[ 1780-40-1 ]

2,4,5,6-Tetrachloropyrimidine

Similarity: 0.85

Chemical Structure| 6554-61-6

[ 6554-61-6 ]

4,5-Dichloropyrimidine

Similarity: 0.85

Chemical Structure| 6554-69-4

[ 6554-69-4 ]

2,4,5-Trichloro-6-methylpyrimidine

Similarity: 0.82

Chemical Structure| 22536-67-0

[ 22536-67-0 ]

2,5-Dichloropyrimidine

Similarity: 0.81

Chemical Structure| 3934-20-1

[ 3934-20-1 ]

2,4-Dichloropyrimidine

Similarity: 0.79

Related Parent Nucleus of
[ 5750-76-5 ]

Pyrimidines

Chemical Structure| 1780-40-1

[ 1780-40-1 ]

2,4,5,6-Tetrachloropyrimidine

Similarity: 0.85

Chemical Structure| 6554-61-6

[ 6554-61-6 ]

4,5-Dichloropyrimidine

Similarity: 0.85

Chemical Structure| 6554-69-4

[ 6554-69-4 ]

2,4,5-Trichloro-6-methylpyrimidine

Similarity: 0.82

Chemical Structure| 22536-67-0

[ 22536-67-0 ]

2,5-Dichloropyrimidine

Similarity: 0.81

Chemical Structure| 3934-20-1

[ 3934-20-1 ]

2,4-Dichloropyrimidine

Similarity: 0.79

; ;