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[ CAS No. 33097-11-9 ] {[proInfo.proName]}

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Chemical Structure| 33097-11-9
Chemical Structure| 33097-11-9
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Product Details of [ 33097-11-9 ]

CAS No. :33097-11-9 MDL No. :MFCD00194954
Formula : C6H4Cl2N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :MRHGOAKYYORQGQ-UHFFFAOYSA-N
M.W : 223.08 Pubchem ID :4614004
Synonyms :
Chemical Name :4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde

Calculated chemistry of [ 33097-11-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.16
TPSA : 68.15 ?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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 2.89
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.227 mg/ml ; 0.00102 mol/l
Class : Soluble
Log S (Ali) : -3.5
Solubility : 0.0699 mg/ml ; 0.000313 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.34
Solubility : 0.102 mg/ml ; 0.000458 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 33097-11-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 33097-11-9 ]

* 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 [ 33097-11-9 ]

[ 33097-11-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 68-12-2 ]
  • [ 1979-98-2 ]
  • [ 33097-11-9 ]
YieldReaction ConditionsOperation in experiment
52% With trichlorophosphate; at 5 - 100℃; for 20h; POCI3 (3.2 mL) was cooled at 5C on an ice bath and supplemented dropwise by dimethylformamide (20 mL, 215 mmol). 2-(Methylthio)pyrimidine-4,6-diol (22e) (5 g, 31.6 mmol) was then added portion-wise and the mixture was stirred at 100C for 20 h. The mixture was poured on crushed ice and extracted with CH2CI2 (3 x 50 mL). The combined organic layers were dried and evaporated to dryness under vacuum.Yield: 52%.Melting point: 87-89C.H NMR (DMSO -d6) d 2.57 (s, 3H, S CH3), 10.07 (s, 1H, CO H).13C NMR (DMSO -d6) d 13.3 (SCH3), 112.9 (C-5), 159.3 (C-4/C-6), 168.2 (C-2), 186.6 (COH).
42% POCI3 (7OmL, 0.75mol) was cooled to -5C and DMF (23mL, 0.3mol) was added slowly. The resultant mixture was allowed to stand at 2O0C for 1 hour. 4,6-dihydroxy-2-methyl- mercaptopyrimidine (15.8 g., 0.1 mol) was added using a solid addition funnel. The reaction mixture was first stirred at room temperature for 30 minutes and then heated at reflux for 3 hours. Following removal of excess POCI3 and DMF in vacuo, the residue was poured into <n="107"/>ice. The solid obtained was filtered and washed with cold water. After treating the solid with hexanes (sonication). the desired product was obtained as a white solid (9.3g, 42%). 1H NMR (CDCl3, 300 MHz) delta 10.34 (s, IH), 2.64 (s, 3H); CHN Calc'd for C6H4Cl2N2OS: C, 32.30; H, 1.81; N, 12.56. Found: C, 32.44; H, 1.69; N, 12.51.
13% With trichlorophosphate; at 10 - 100℃; Reference Example 69 Production of 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde To ice-cooled phosphorus oxychloride (77.62 g, 506 mmol) was added dropwise DMF (9.29 mL, 120 mmol), and the mixture was stirred at room temperature for 1 hr. 2-(Methylsulfanyl)pyrimidine-4,6-diol (15.8 g, 100 mmol) was added thereto by small portions, and the mixture was stirred at room temperature for 1 hr, at 40-50C for 1 hr, and then at 100C overnight. After cooling, the reaction mixture was poured into ice, and the mixture was extracted twice with ethyl acetate. The extract was washed successively with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=95:5?85:15) to give the title compound (2.97 g, 13%) as a pale-yellow solid. 1H NMR (300 MHz, CDCl3) delta:2.64 (3 H, s), 10.38 (1 H, s).
Step 1. Preparation of 4,6-Dichloro-2-methylsulfsanyl-pyrimidine-5-carbaldehyde Phosphorous oxychloride (213 mL, 2.3 mol) was cooled in a sodium chloride-water ice bath to 1.8 C. under nitrogen. Dimethyl formamide (71.4 mL, 0.92 mol) was added dropwise over 45 minutes with stirring. The reaction mixture was allowed to warm up to room temperature and was stirred at room temperature for 30 minutes, and followed by stirring at 40 C. for 20 minutes. The reaction mixture was then heated to 57 C., and 2-Methylsulfanyl-pyrimidine-4,6-diol (50.0 g, 0.307 mol) was added in 5.0 g portions over 90 minutes. The reaction mixture was stirred for one hour at 55 C., and then heated to 110 C. with stirring for 17.5 hours. The reaction mixture was cooled and volatiles were removed under reduced pressure. The residue was poured into one lire of ice water. The resulting precipitate was isolated by filtration, washed with water, then with heptanes, and was dried to provide 25.2 g of crude 4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde. Mass Spec. M+H=224.
With trichlorophosphate; at 1.8 - 110℃; for 20.5h; Phosphorous oxychloride (213 mL, 2.3 mol) was cooled in a sodium chloride-water ice bath to 1.8 C. under nitrogen. Dimethyl formamide (71.4 mL, 0.92 mol) was added dropwise over 45 minutes with stirring. The reaction mixture was allowed to warm up to room temperature and was stirred at room temperature for 30 minutes, and followed by stirring at 40 C. for 20 minutes. The reaction mixture was then heated to 57 C., and 2-Methylsulfanyl-pyrimidine-4,6-diol (50.0 g, 0.307 mol) was added in 5.0 g portions over 90 minutes. The reaction mixture was stirred for one hour at 55 C., and then heated to 110 C. with stirring for 17.5 hours. The reaction mixture was cooled and volatiles were removed under reduced pressure. The residue was poured into one litre of ice water. The resulting precipitate was isolated by filtration, washed with water, then with heptanes, and was dried to provide 25.2 g of crude 4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde. Mass Spec. M+H=224.
With trichlorophosphate; at 30℃; for 4h;Heating / reflux; 4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde. DMF (7 mL, 91 mmol) was slowly added to POCl3 (22 ml, 240 mmol) maintaining the temperature below 300C. To the resultant solution was added 2-methylsulfanyl-pyrimidine-4,6-diol (7.06 g, 44.6 mmol) maintaining the temperature below 300C. The resultant slurry was heated to reflux for 4 h. The solvent was removed and the residue was poured onto ice and extracted with EtOAc, dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% ethyl acetate in hexanes) gave the desired product. ESIMS calcd 224 (M+ + H), found 224 (M+ + H).

  • 2
  • [ 33097-11-9 ]
  • [ 85426-79-5 ]
YieldReaction ConditionsOperation in experiment
95% With hydrazine hydrate; triethylamine; In tetrahydrofuran; at 5℃; for 1h; To a suspension of (27i) (2.5 g, 11.2 mmol) in THF (25 mL) cooled at 5C on an ice bath, were added dropwise hydrazine monohydrate (0.65 mL, 13 mmol) and triethylamine (1.8 mL, 13 mmol). After 1 hour stirring at 5C, the mixture was evaporated to dryness under vacuum and the residue was purified by silica gel column chromatography.Yield: 95%.Melting point: >300C.H NMR (DMSO -d6) d 2.59 (s, 3H, S CH3), 8.32 (s, 1H, CH), 14.25 (bs, 1H, N H).13C NMR (DMSO -d6) d 13.9 (SCH3), 109.6 (C-3a), 133.1 (C-3), 152.9-155.4 (C-4/C-7a), 168.7 (C- 6).
With N-ethyl-N,N-diisopropylamine; hydrazine; In 1,4-dioxane; at 0℃; for 1088h;Heating / reflux;Product distribution / selectivity; Step 2. Preparation of4-Chloro-6-methylsulfanyl-lH-pyrazolo[3,4-d]pyrimidine; 4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (7.54 g, 0.0338 mol) was added to 80 mLof dioxane and stirred for 10 min at RT. Diisopropyl ethylamine (6.03 mL, 0.0340 mol) was added and the mixture was cooled in an ice bath with stirring for 10 min. Anhydrous hydrazine (1.08 mL, 0.0338 mmol) was added dropwise over three min, and stirring was continued for an additional five min. The ice bath was removed, and the reaction mixture was heated to reflux with stirring for 2 hours. The reaction mixture was then stirred at RT for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added to 20 mL of 2 N HCl and 100 mL EtOAc. The result- ing suspension was stirred and filtered, ad the solid was washed with water followed by EtOAc. The organic phase of the filtrate was collected, and the aqueous phase was extracted three times with 150 mL EtOAc. The combined organic phases were dried (MgSO4), filtered, and the filtrate was evaporated under reduced pressure. The resulting solid was washed with diethyl ether/hexanes (1:1) and the solid was dried to provide 3.13 g of crude 4-Chloro-6-methylsulfanyl-lH-pyrazolo[3,4-d]pyrimidine. Mass Spec. M-I-H = 201.Step 2. Preparation of4-Chloro-6-methylsulfanyl-lH-pyrazolo[3,4-d]pyrimidine; 4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (7.54 g, 0.0338 mol) was added to 80 mL of dioxane and stirred for 10 min at RT. Diisopropyl ethylamine (6.03 mL,0.0340 mol) was added and the mixture was cooled in an ice bath with stirring for 10 min. Anhydrous hydrazine (1.08 mL, 0.0338 mmol) was added dropwise over three min, and stirring was continued for an additional five min. The ice bath was removed, and the reaction ixture was heated to reflux with stirring for two hours. The reaction mixture was then stirred at RT for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added to 20 mL of 2 N HCl and 100 mL EtOAc. The resulting suspension was stirred and filtered, ad the solid was washed with water followed by EtOAc. The organic phase of the filtrate was collected, and the aqueous phase was extracted three times with 150 mL EtOAc. The combined organic phases were dried (MgSO4), filtered, and the filtrate was evaporated under reduced pressure. The resulting solid was washed with diethyl ether/hexanes (1:1) and the solid was dried to provide 3.13 g of crude 4-Chloro-6-methylsulfanyl-lH-pyrazolo[3,4-d]pyrimidine. Mass Spec. M+H = 201.
Step 2. Preparation of 4-Chloro-6-methylsulfanyl-]H-pyrazolo[3,4-d]pyrimidine 4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (7.54 g, 0.0338 mol) was added to 80 mL of dioxane and stirred for 10 minutes at room temperature. Diisopropyl ethylamine (6.03 mL, 0.0340 mol) was added and the mixture was cooled in an ice bath with stirring for 10 minutes. Anhydrous hydrazine (1.08 mL, 0.0338 mmol) was added dropwise over three minutes, and stirring was continued for an additional five minutes. The ice bath was removed, and the reaction ixture was heated to reflux with stirring for two hours. The reaction mixture was then stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added to 20 mL of 2 N HCl and 100 mL EtOAc. The resulting suspension was stirred and filtered, ad the solid was washed with water followed by EtOAc. The organic phase of the filtrate was collected, and the aqueous phase was extracted three times with 150 mL EtOAc. The combined organic phases were dried (MgSO4), filtered, and the filtrate was evaporated under reduced pressure. The resulting solid was washed with diethyl ether/hexanes (1:1) and the solid was dried to provide 3.13 g of crude 4-Chloro-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine. Mass Spec. M+H =201.
With N-ethyl-N,N-diisopropylamine; hydrazine; In 1,4-dioxane; ethyl acetate; at 0 - 20℃; for 18.5h;Heating / reflux; 4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (7.54 g, 0.0338 mol) was added to 80 mL of dioxane and stirred for 10 minutes at room temperature. Diisopropyl ethylamine (6.03 mL, 0.0340 mol) was added and the mixture was cooled in an ice bath with stirring for 10 minutes. Anhydrous hydrazine (1.08 mL, 0.0338 mmol) was added dropwise over three minutes, and stirring was continued for an additional five minutes. The ice bath was removed, and the reaction ixture was heated to reflux with stirring for two hours. The reaction mixture was then stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added to 20 mL of 2 N HCl and 100 mL EtOAc. The resulting suspension was stirred and filtered, ad the solid was washed with water followed by EtOAc. The organic phase of the filtrate was collected, and the aqueous phase was extracted three times with 150 mL EtOAc. The combined organic phases were dried (MgSO4), filtered, and the filtrate was evaporated under reduced pressure. The resulting solid was washed with diethyl ether/hexanes (1:1) and the solid was dried to provide 3.13 g of crude 4-Chloro-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine. Mass Spec. M+H=201.

  • 3
  • [ 1979-98-2 ]
  • [ 33097-11-9 ]
YieldReaction ConditionsOperation in experiment
61% 57a) 4-chloro-6-[(2,6-difluorophenyDamino]-2-(methylthio')-5- pyrimidinecarbonitrile; To the solution of phosphorus oxychloride (65 mL, 0.70 mol) in trichloroethylene (46.5 mL) was added DMF (25 mL, 0.32 mol) slowly to keep the temperature between 5 0C to 10 0C. The solution was then warmed up to room temperature before 6-hydroxy-2-(methylthio)-4(l/i)-pyrimidinone (25 g, 0.16 mol) was added in portions. The resultant reaction mixture was heated at 80 0C overnight followed by concentration under vacuum. The resulting slurry like residue was poured into ice, stirred for about 2 hours then filtered to afford the crude product. The crude product was further purified by recrystalization with hexane to afford 4,6- dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde (21.3 g , 61%). 1H-NMR (CDCl3) delta 2.66 (s, 3 H), 10.4 (s, I H).
61% Example 1; N-CcvclopropylmethylV3-r8-r2,6-difluororhohenylV2-(r2-hvdroxy-l- rhvdroxymethv?ethyl"|amino)-7-oxo-718-dihvdropyridor2,3-dlpyrimidin-4-yl)-4- methylbenzamidela) 4-chloro-8-(2.6-difluorophenyl)-2-('methylthio)pyridor2.3-^)pyrimidin-7r8Hr)- oneTo the solution of phosphorus oxychloride (65 mL, 0.70 mol) in trichloroethylene (46.5 mL) was added DMF (25 mL, 0.32 mol) slowly to keep the temperature between 5 0C to 10 0C. The solution was then warmed up to room temperature before 6-hydroxy-2- (methylthio)-4(lH)-pyrimidinone (25 g, 0.16 mol) was added in portions. The resultant reaction mixture was heated at 80 0C overnight followed by concentration under vacuum. The resulting slurry like residue was poured into ice, stirred for 2 hours then filtered to afford the crude product. The crude product was further purified by recrystalization with hexane to afford 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde (21.3 g , 61%). 1H-NMR (CDCl3) delta 2.66 (s, 3 H), 10.4 (s, 1 H).
Example 11: Synthesis of 6-(2,4-Difluoro-phenoxy)-3-iodo-lH-pyrazolo[3,4-d]pyri- midine; Step 1. Preparation of4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde; Phosphorous oxychloride (213 mL, 2.3 mol) was cooled in a sodium chloride- water ice bath to 1.8 0C under nitrogen. Dimethyl formamide (71.4 mL, 0.92 mol) was added drop- wise over 45 min with stirring. The reaction mixture was allowed to warm up to RT and was stirred at RT for 30 min, and followed by stirring at 400C for 20 min. The reaction mixture was then heated to 570C, and 2-Methylsulfanyl-pyrimidine-4,6-diol ( 50.0 g, 0.307 mol) was added in 5.0 g portions over 90 min. The reaction mixture was stirred for one hour at 55 0C, and then heated to 1100C with stirring for 17.5 hours. The reaction mixture was cooled and volatiles were removed under reduced pressure. The residue was poured into one litre of ice water. The resulting precipitate was isolated by filtration, washed with water, then with heptanes, and was dried to provide 25.2 g of crude 4,6-Dichloro-2- methylsulfanyl-pyrimidine-5-carbaldehyde. Mass Spec. M+H = 224.Example 19: Synthesis of (i?)-l-[6-(2,4-Difluoro-phenoxy)-3-(2-ethoxy-5-fluoro- phenyl)-lH-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-olStep 1.; Preparation of4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde; Phosphorous oxychloride (213 mL, 2.3 mol) was cooled in a sodium chloride- water ice bath to 1.8 0C under nitrogen. Dimethyl formamide (71.4 mL, 0.92 mol) was added drop- wise over 45 min with stirring. The reaction mixture was allowed to warm up to RT and was stirred at RT for 30 min, and followed by stirring at 400C for 20 min. The reaction mixture was then heated to 570C, and 2-Methylsulfanyl-pyrimidine-4,6-diol ( 50.0 g, 0.307 mol) was added in 5.0 g portions over 90 min. The reaction mixture was stirred for one hour at 55 0C, and then heated to 1100C with stirring for 17.5 hours. The reaction mixture was cooled and volatiles were removed under reduced pressure. The residue was poured into one litre of ice water. The resulting precipitate was isolated by filtration, washed with EPO <DP n="71"/>water, then with heptanes, and was dried to provide 25.2 g of crude 4,6-Dichloro-2- methylsulfanyl-pyrimidine-5-carbaldehyde. Mass Spec. M+H = 224.
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; ;