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CAS No. : | 2915-15-3 | MDL No. : | MFCD00297223 |
Formula : | C11H9ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MKRVYJDOHARDKT-UHFFFAOYSA-N |
M.W : | 204.66 | Pubchem ID : | 796128 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.09 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.44 |
TPSA : | 25.78 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.26 cm/s |
Log Po/w (iLOGP) : | 2.5 |
Log Po/w (XLOGP3) : | 3.23 |
Log Po/w (WLOGP) : | 3.11 |
Log Po/w (MLOGP) : | 2.16 |
Log Po/w (SILICOS-IT) : | 3.58 |
Consensus Log Po/w : | 2.91 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.71 |
Solubility : | 0.0397 mg/ml ; 0.000194 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.44 |
Solubility : | 0.0736 mg/ml ; 0.000359 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.18 |
Solubility : | 0.00136 mg/ml ; 0.00000664 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.89 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; isopropyl alcohol at 83℃; for 18 h; Inert atmosphere; Sealed tube | General procedure: To a degassed solution of4,6-dichloropyrimidine (200 mg, 1.0 equiv) and arylboronic acid (1.0 equiv) in iPrOH (4 mL) in a 20 mLmicrowave vial was added an aqueous solution of 2M Na2CO3 (2.5 equiv) and Pd(PPh3)4 (5.0 molpercent)under an argon atmosphere and the resulting heterogeneous solution was further degassed for 10 min. Thevial was sealed and placed in an oil bath at 83 oC and the reaction mixture was refluxed for 18 h, cooled,diluted with H2O (20 mL) and the whole was extracted with EtOAc (3 X 30 mL). The combined organicextract was washed with brine, dried (Na2SO4), and evaporated under reduced pressure give an oil whichwas purified by gradient column chromatography on silica gel using EtOAc/hexanes as eluent to affordcompounds 9a-j. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Stage #1: for 20 h; Heating / reflux Stage #2: With sodium hydrogencarbonate In water; ethyl acetate |
Step-2; 4-Chloro-2-methyl-6-phenylpyrimidine; A mixture of 2-methyl-6-phenylpyrimidin-4(3H)-one (15g) and POCl3 (150ml) was refluxed under nitrogen for 2Oh. The excess POCI3 was distilled off and the residue was diluted with ethyl acetate (500ml) and washed with 10percent solution of sodium bicarbonate (100ml), water, brine and dried. The solvent was removed under reduced pressure and the residue was purified by chromatography (silica, 60-120 mesh) eluting with pet ether / ethyl acetate (9/1) to afford 1 Ig (67percent) of the titled as a pale yellow solid.MP: 57-590C, MS: Mass found (M+l, 204.9), 1H NMR (DMSO-c/(5,400 MHz) δ 2.50 (3H, s), 7.52-7.58 (3H, m), 8.08 (IH, s), 8.20-8.22 (2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | for 3 h; Heating / reflux | EXAMPLE 10; 4-Methoxyphenyl)-methyl-(2-methyl-6-phenyl-pyrimidin-4-yl) amine.; [00107] A mixture of ethyl benzylacetate 1.92g (10.0 mmol) and acetamidine hydrochloride 5.Og (53.0 mmol) with a ethanol solution (23percent wt) of EtONa 2OmL (67.5 mmol) was stirred for 36h under reflux. After removal of ethanol, the crude product was extracted with EtOAc, washed with water, and dried on anhydrous MgSO4. After removal of solvents, the intermediate 2-methyl-6- phenylpyrimidin-4-ol was dried under reduced pressure, and used without further purification. A mixture of 2-methyl-6-phenylpyrimidin-4-ol 0.93 g (5.0 mmol) and POCI3 5 mL was heated under reflux for 3 h. After cooling, excess of POCI3 was removed under reduced pressure, and the crude product was diluted with CHCI3. The solution was poured into ice-water, washed with water, and dried on anhydrous MgSO4. Removal of CHCI3 gave 4-chloro-2-methyl-6-phenylpyrimidine (EMI-mass: 206 [M]+) in 90percent yield (98percent purity). A solution of 4-chloro-2-methyl-6- phenylpyrimidine 0.206 g (1.0 mmol) and 4-methoxy-N-methylaniline 0.137 g (1.0 mmol) with cone. HCl 0.2 mL in zsoe-propanol 5 mL was stirred at 23 0C for 16 h. The solution was concentrated under reduced pressure, diluted with CH2Cl2 30 mL, washed with sat. νa2Cψ3 aqueous solution, and dried on anhydrous MgSO4. After removal of solvents, the crude product was purified with gradient column chromatography (EtOAc/hexanes, 0percent to 60percent) to give titled product in 80percent yield. 1H NMR (CD3OD, 400 MHz): δ 7.80-7.76 (m, 2H), 7.39-7.36 (m, 3H), 7.22 (d, 2H, J = 9.0 Hz), 6.99 (d, 2H, J = 9.0 Hz), 6.40 (s, IH), 3.86 (s, 3H), 3.51 (s, 3H), 2.66 (s, 3H). m/e: 306.2506 (M+l). |
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