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CAS No. : | 89466-42-2 | MDL No. : | MFCD10574952 |
Formula : | C6H7ClN2OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FNYLFWGITLMOHA-UHFFFAOYSA-N |
M.W : | 190.65 | Pubchem ID : | 9836999 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.26 |
TPSA : | 60.31 Ų |
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) : | -5.82 cm/s |
Log Po/w (iLOGP) : | 2.46 |
Log Po/w (XLOGP3) : | 2.31 |
Log Po/w (WLOGP) : | 1.86 |
Log Po/w (MLOGP) : | 0.55 |
Log Po/w (SILICOS-IT) : | 2.06 |
Consensus Log Po/w : | 1.85 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.75 |
Solubility : | 0.34 mg/ml ; 0.00178 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.21 |
Solubility : | 0.116 mg/ml ; 0.00061 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.9 |
Solubility : | 0.242 mg/ml ; 0.00127 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.08 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
78% | With Oxone®; tetrabutylammomium bromide In water; acetone at 20℃; | General procedure: A mixture of 2-(methylthio)pyrimidines (5 mmol), tetrabutylammonium bromide (0.16 g, 0.5 mmol, 10 molpercent) and acetone (20 mL) was stirred at room temperature. The Oxone (12.5 mmol, 2.5 equiv) in water (20 mL) was added slowly to the vigorously stirred solution. After 4–6 h, TLC indicated the consumption of the starting material. The products 5 were isolated by filtering through a Buechner funnel and washed with water, and then dried to give the solid product. Yields, melting points and spectroscopic data for selected 2-(methylsulfonyl)pyrimidines are listed as follows. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | at 20℃; | To a solution of sodium (0.28 g, 12 mmol) in ethanol 20 mL was added in 4,6-dichloro-2-(methylthio)pyrimidine 4a (1.95g, 10 mmol) and the resulting mixture was stirred at room temperature until disappearance of the starting material 4a as judged by TLC. The mixture was evaporated under reduced pressure, water was added, and after workup (CH2Cl2 extraction, water washing, Na2SO4 drying of the organic phase), the residue was evaporated under reduced pressure, and the residue was recrystallized from ethylether yielded the desired product 4g. White solid, yield 70percent, m.p. 39-40 °C; IR (KBr, cm-1): 3003, 2939, 1544, 1328, 1274, 1505, 1030, 820; 1H NMR (400 MHz, CDCl3) δ: 2.55 (s, 3H, SCH3), 3.97 (s, 3H, OCH3), 6.41 (s, 1H, pyrimidine-H). 13C NMR (100 MHz, CDCl3): δ 14.29,54.52, 102.43, 160.34, 169.90, 172.92; LC-MS (m/z): 190.0. Anal. Calcd for C6H7ClN2OS: C, 37.80; H, 3.70; N, 14.69. Found: C, 37.72; H, 3.75; N, 14.78. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | at 35℃; for 1 h; | c. 4-Chloro-6-(methyloxy)-2-(methylthio)pyrimidine (IX) To a solution of 4,6-dichloro-2-(methylthio)pyrimidine (7.8 g, 40 mmol) in MeOH (100 mL), NaOMe (4.1 M in MeOH, 10.2 mL) was added at 35° C. and stirred at same temperature for 1 hr. After evaporation, the mixture was extracted with CH2Cl2 and washed with water. The organic layer was dried over Na2SO4 then evaporated. The residue was purified on SiO2 chromatography to give the title compound (5.8 g, 75percent); MS (ESI) (M+H)+ 192. Example 37; 6-(1,3-Benzodioxol-5-yl)-2-(1H-indazol-5-ylamino)-4(1H)-pyrimidinone (Iak); a. 4-Chloro-6-(methyloxy)-2-(methylthio)pyrimidine To a solution of 4,6-dichloro-2-(methylthio)pyrimidine (7.8 g, 40 mmol) in MeOH (100 mL), NaOMe (4.1 M in MeOH, 10.2 mL) was added at 35° C. and stirred at same temperature for 1 hr. After evaporation, the mixture was extracted with CH2Cl2 and washed with water. The organic layer was dried over Na2SO4 then evaporated. The residue was purified on SiO2 chromatography to give the title compound (5.8 g, 75percent); MS (ESI) (M+H)+ 192. |
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