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[ CAS No. 1046816-75-4 ] {[proInfo.proName]}

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Chemical Structure| 1046816-75-4
Chemical Structure| 1046816-75-4
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Quality Control of [ 1046816-75-4 ]

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Product Details of [ 1046816-75-4 ]

CAS No. :1046816-75-4 MDL No. :MFCD16659172
Formula : C5H5ClN2O Boiling Point : No data available
Linear Structure Formula :- InChI Key :OHMILAMAADHENX-UHFFFAOYSA-N
M.W : 144.56 Pubchem ID :54150633
Synonyms :

Calculated chemistry of [ 1046816-75-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.17
TPSA : 46.01 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 0.28
Log Po/w (WLOGP) : 0.47
Log Po/w (MLOGP) : -0.34
Log Po/w (SILICOS-IT) : 1.42
Consensus Log Po/w : 0.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.34
Solubility : 6.61 mg/ml ; 0.0457 mol/l
Class : Very soluble
Log S (Ali) : -0.81
Solubility : 22.5 mg/ml ; 0.156 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.08
Solubility : 1.22 mg/ml ; 0.00841 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 1046816-75-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1046816-75-4 ]

* 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 [ 1046816-75-4 ]

[ 1046816-75-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 287714-35-6 ]
  • [ 1046816-75-4 ]
YieldReaction ConditionsOperation in experiment
To a dry flask was added methyl 2-chloropyrimidine-5-carboxylate (17 mg) and THF (5 mL). The mixture was cooled to -780C and a solution of DIBAL-H in hexane (1 M, 1.2 mL) was added slowly. The resulting mixture was stirred at -780C to it overnight, then quenched with saturated aqueous Na2SO4. The solution was filtered. Solvents were removed under reduced pressure to give (2-chloropyrimidin-5-yl)methanol. MS calcd. for [M+H]+ CsH6ClN2O: 145.1; found: 145.1.
A solution of 2-chloropyrimidine-5-carboxylic acid methyl ester (l .Og, 5.8mmol) in THF (30mL), under argon, was cooled to -78°C. To the solution was added a solution of DIBAL-H in DCM (1.0M, 20.3mL, 20.3mmol), slowly over 40min. The reaction was allowed to warm to r. t. before continuing to stir for a further 16 h. A solution of sat. sodium potassium tartrate (lOOmL) was slowly added, followed by EtOAc, and the mixture was stirred vigorously for 2 h. The organic phase was separated then a further portion of EtOAc was added to the aquoues phase before stirring vigorously for lh. The organic phase was removed and the aqueous phase was washed with a mixture of EtOAc and THF (1 :1). All organic fractions were combined and washed with sat. sodium potassium tartrate solution, water, then brine, and dried (MgS04). The solvent was removed in vacuo to afford the title compound: RT = 1.62 min; mlz (ES+) = 145.0 [M+ H]+.
  • 2
  • [ 1046816-75-4 ]
  • [ 1046816-67-4 ]
  • [ 1046814-96-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 160℃; for 0.166667h;microwave irradiation; To a reaction vessel was added 2- (methylsulfonyl)-6-(3-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)propoxy)- 1,2,3,4-tetrahydroisoquinoline (20 mg), <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (10 mg), Pd(PPh3)4 (2 mg), dioxane (2 mL) and Na2CO3 (1 M, 1 mL). The mixture was irradiated in a microwave at 16O0C for 10 min. The mixture was cooled to rt, extracted with CHCl3. The extracts were combined, washed with water, dried (MgSO4) and filtered. Solvents were removed under reduced pressure to give crude product. Purification of the crude on silica gel column (EtOAc: Hexanes = 2: 1) afforded the desired product. MS calcd. for [M+H]+ C25H29N2O4S: 453.2; found: 453.2.
  • 3
  • [ 1046816-75-4 ]
  • (4-methoxy-2-(trifluoromethyl)phenyl)boronic acid [ No CAS ]
  • [ 1186482-23-4 ]
YieldReaction ConditionsOperation in experiment
Pd(PPh3)4; In toluene; [2-(4-Methoxy-2-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol A mixture of <strong>[1046816-75-4](2-Chloro-pyrimidin-5-yl)-methanol</strong> (350 mg, 5.81 mmol), 4-Methoxy-2-trifluoromethyl-phenylboronic acid (700 mg, 1.2 eq.) Pd(PPh3)4 (5 mol percent) in toluene (10 mL) and Na2CO3 (aq. 2N, 4 mL) was sparged with argon and refluxed for 60 minutes. The reaction was cooled, partitioned between EtOAc and water and the organics dried with brine and Na2SO4. The crude product was purified by silica gel chromatography eluding with 80percent EtOAc: hexanes. MS 285 (M+H+).
  • 4
  • [ 120747-85-5 ]
  • [ 1046816-75-4 ]
YieldReaction ConditionsOperation in experiment
In hydrogenchloride; (2-Chloro-pyrimidin-5-yl)-methanol A solution of <strong>[120747-85-5](2-Amino-pyrimidin-5-yl)-methanol</strong> (400 mL, 3.2 mmol) was dissolved in HCl (aq. 3M, 20 mL) and treated with NaNO2 (aq. 1N, 20 mL). The reaction was stirred at 0° C. for 18 hours. The mixture was basified with K2CO3 (aq.) then extracted with DCM (3*50 mL). The organics were washed with more K2CO3 (aq.) and the organics concentrated to give the pure product as needles.
  • 5
  • [ 1046816-75-4 ]
  • [ 1272973-58-6 ]
  • [ 1272974-11-4 ]
YieldReaction ConditionsOperation in experiment
43% Diisopropyl azodicarboxylate (0.140 mL, 0.71 mmol) was added to a stirred solution of tert-butyl 4-(5-hydroxypyrimidin-2-yl)piperazine-1-carboxylate (0.16 g, 0.57 mmol), and triphenylphosphine (0.225 g, 0.86 mmol) in THF (5 mL) under nitrogen. The resulting solution was stiffed at 20° C. for 30 minutes and then <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (0.083 g, 0.57 mmol) was added. The resulting solution was stirred at rt for 24 hours under nitrogen. The solvent was evaporated and the residue diluted with EtOAc and brine. A white ppt was filtered off and dried under vacuum. The aqueous layer was extracted with EtOAc (50 mL) and the combined organics were concentrated in vacuo to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 1 to 4percent MeOH in DCM. The crude product was purified by flash silica chromatography, elution gradient 40 to 100percent EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(5-((2-chloropyrimidin-5-yl)methoxy)pyrimidin-2-yl)piperazine-1-carboxylate (0.100 g, 43percent) as a white solid. 1H NMR (400.132 MHz, CDCl3) 1.49 (9H, s), 3.47-3.52 (4H, m), 3.71-3.75 (4H, m), 5.02 (2H, s), 8.14 (2H, s), 8.69 (2H, s). m/z (ES+) (M+H)+=407; HPLC tR=3.18 min.
  • 6
  • [ 1046816-75-4 ]
  • [ 1245079-22-4 ]
  • [ 1351341-74-6 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 70℃; for 21h; To a dry solution of <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (Preparation 74, 253mg, 1.75mmol) and [(3i?,45)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester (Preparation 48, 574mg, 1.93mmol) in DMSO (1.6mL) was added DBU (262muEpsilon,1.75mmol) and the reaction was heated to 70°C for 21 h. The mixture was diluted with water and extracted with EtOAc (x 2). The organic fractions were combined, washed with sat. NaHC03 solution, then brine, and dried (MgS04). Removal of the solvent in vacuo and purification by column chromatography (DCM:MeOH, 97:3) afforded the title compound: RT = 3.23 min; mlz (ES+) = 407.1 [M+ H]+.
  • 7
  • [ 1046816-75-4 ]
  • [ 74-88-4 ]
  • [ 1416366-34-1 ]
YieldReaction ConditionsOperation in experiment
66% With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.833333h; To a solution of <strong>[1046816-75-4]2-chloro-5-hydroxymethyl-pyrimidine</strong> (9.0 g, 62 mmol) in 70 ml of anhydrous DMF was added methyl iodide (6 eq. 370 mmol, 23 ml). The mixture was cooled to 0°C, then NaH (2.6 lg, 1.05 eq.) was added in portions over 5 mins. The resulting mixture was stirred 25 min. at 0°C, then 25 min. at rt. The reaction mixture was then cooled in ice bath, and quenched by addition of saturated NH4C1 aq. solution (200 ml ), extracted with ether (150 ml x 3). The combined organic layers were washed by brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by ISCO column (330 g of silica gel) using ethyl acetate in hexane (0-90percent ethyl acetate, 2500 ml, then 1000 ml of ethyl acetate) to give 6.5g (66percent) of the title compound: MS (ESI) mlz 159.2 (M+H); 1H NMR (500 MHz, CDC13) delta 8.60 (s, 2H), 4.48 (s, 2H), 3.45 (s, 3H).
66% With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.916667h; To a solution of <strong>[1046816-75-4]2-chloro-5-hydroxymethyl-pyrimidine</strong> (9.0 g, 62 mmol) in 70 ml of anhydrous DMF was added methyl iodide (6 eq. 370 mmol, 23 ml). The mixture was cooled to 0°C, then NaH (2.6 lg, 1.05 eq.) was added in portions over 5 mins. The resulting mixture was stirred 25 min. at 0°C, then 25 min. at rt. The reaction mixture was then cooled in ice bath, and quenched by addition of saturated NH4CI aq. solution (200 ml ), extracted with ether (150 ml x 3). The combined organic layers were washed by brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by ISCO column (330 g of silica gel) using ethyl acetate in hexane (0-90percent ethyl acetate, 2500 ml, then 1000 ml of ethyl acetate) to give 6.5g (66percent) of the title compound: MS (ESI) mlz 159.2 (M+H); NMR (500 MHz, CDC13) delta 8.60 (s, 2H), 4.48 (s, 2H), 3.45 (s, 3H).
66% With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.833333h; To a solution of<strong>[1046816-75-4]2-chloro-5-hydroxymethyl-pyrimidine</strong> (9.0 g, 62 mmol) in 70 ml ofanhydrous DMF was added methyl iodide (6 eq. 370 mmol, 23 ml). The mixture was cooled to0°C, then NaH (2.61g, 1.05 eq.) was added in portions over 5 mins. The resulting mixture wasstirred 25 min. at 0°C, then 25 min. at rt. The reaction mixture was then cooled in ice bath, and10 quenched by addition of saturated NH4Cl aq. solution (200 ml ), extracted with ether (150 ml x3). The combined organic layers were washed by brine, dried over Na2S04, filtered andconcentrated in vacuo. The residue was purified by ISCO column (330 g of silica gel) usingethyl acetate in hexane (0-90percent ethyl acetate, 2500 ml, then 1000 ml of ethyl acetate) to give 6.5g(66percent) of the title compound: 1H NMR (500 MHz, CDCh) 8 8.60 (s, 2H), 4.48 (s, 2H), 3.45 (s,15 3H). MS ESI m/z 159.2 (M+H).
Preparation of 2-chloro-5-methoxymethylpyrimidine 18To a solution of <strong>[1046816-75-4]2-chloro-5-hydroxymethyl-pyrimidine</strong> (9.0 g, 62 mmol) in 70 ml of anhydrous DMF was added methyl iodide (6 eq. 370 mmol, 23 ml). The mixture was cooled to 0°C, then NaH (2.6 lg, 1.05 eq.) was added in portions over 5 mins. The resulting mixture was stirred 25 min. at 0°C, then 25 min. at rt. The reaction mixture was then cooled in ice bath, and quenched by addition of saturated NH4C1 aq. solution (200 ml ), extracted with ether (150 ml x 3). The combined organic layers were washed by brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by IS CO column (330 g of silica gel) using ethyl acetate in hexane (0-90percent ethyl acetate, 2500 ml, then 1000 ml of ethyl acetate) to give 6.5g (66percent) of the title compound: MS (ESI) mlz 159.2 (M+H); 1H NMR (500 MHz, CDC13) delta 8.60 (s, 2H), 4.48 (s, 2H), 3.45 (s, 3H).

  • 8
  • [ 1046816-75-4 ]
  • [ 1416365-78-0 ]
  • 9
  • [ 1046816-75-4 ]
  • [ 1416365-82-6 ]
  • 10
  • [ 1046816-75-4 ]
  • {trans-4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrimidin-2-yloxy]-cyclohexyl}-acetic acid methyl ester [ No CAS ]
  • methyl (trans-4-[5-(hydroxymethyl)-2,5'-bipyrimidin-2'-yl]oxy}cyclohexyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In water; N,N-dimethyl-formamide; at 120℃; for 1.33333h;Sealed tube; Microwave irradiation; (2-Chloropyrimidin-5-yl)methanol (0.49g, 3.39 mmol, 1.0 equiv.), {trans-4-[5- (4,4,5,5-Tetramethyl-l ,3,2-dioxaborolan-2-yl)-pyrimidin-2-yloxy]-cyclohexyl}-acetic acid methyl ester (1.275 g, 3.39 mmol, 1 equiv.), Pd(dppf) (0.124 g, 0.169 mmol, 0.05equiv.), and 2 Na2C03 (aq) (5.48 mL, 10.95 mmol, 4 equiv.) were placed in DMF (15 mL) and stirred at room temperature in a sealed microwave reaction vial. The reaction was placed under vacuum for 5 min (until no continuing gas evolution was detected) and then 2 (g) was bubbled into the reaction suspension for 25 min. The reaction suspension was heated at 120°C under microwave conditions for 1 hr 20 min. The reaction was concentrated to a residue which was then dissolved in EtOAc / brine. The EtOAc phase was dried over Na2SC>4, filtered, and concentrated to an oil. Purification with Biotage SP-1 [ FLASH 25 cartridge. Hexanes:EtOAc 0>12percent 2CV; 12> 100percent 10CV; 100percent 5CV ] to afford methyl (tran5-4-[5-(hydroxymethyl)-2,5'-bipyrimidin-2'-yl]oxy}cyclohexyl)acetate. LC-MS (ES, m/z): C 17H20N4O4: 344; Found: 344 [M+H]+.
  • 11
  • [ 1046816-75-4 ]
  • {trans-4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrimidin-2-yloxy]-cyclohexyl}-acetic acid methyl ester [ No CAS ]
  • methyl (trans-4-[5-formyl-2,5'-bipyrimidin-2'-yl]oxy}cyclohexyl)acetate [ No CAS ]
  • 12
  • [ 1046816-75-4 ]
  • [ 75-03-6 ]
  • [ 1437778-96-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.5h;Cooling with ice; A solution of the <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (1 g, 6.92 mmol) in anhydrous DMF (6.92 ml) was cooled at ice-bath temperature and iodoethane (2.236 ml, 27.7 mmol) added. The solution was stirred for 10 minutes at 0°C. Sodium hydride (0.304 g, 7.61 mmol) was added and the resulting mixture stirred at 0°C for 0.5 hours and RT for 60 minutes. The mixture was diluted with saturated ammonium chloride (100 mL) and extracted with EtOAc (3 x 50 mL). The organic fractions were combined, washed with brine (100 mL), dried over Na2S04, filtered and the volatiles removed in vac. The mixture was purified on a 50 g Biotage KP-Si02 cartridge using a gradient eluant of 0-100percent EtOAc:Hexanes, to afford the title compound. LC/MS (m/z): 173(M+H)+-
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; ;