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CAS No. : | 19858-50-5 | MDL No. : | MFCD11053756 |
Formula : | C6H8N2OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZEIJWLQVULZDCE-UHFFFAOYSA-N |
M.W : | 156.21 | Pubchem ID : | 22050485 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 39.88 |
TPSA : | 71.31 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.14 cm/s |
Log Po/w (iLOGP) : | 1.62 |
Log Po/w (XLOGP3) : | 0.16 |
Log Po/w (WLOGP) : | 0.54 |
Log Po/w (MLOGP) : | -0.34 |
Log Po/w (SILICOS-IT) : | 1.26 |
Consensus Log Po/w : | 0.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.22 |
Solubility : | 9.38 mg/ml ; 0.0601 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.21 |
Solubility : | 9.53 mg/ml ; 0.061 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.97 |
Solubility : | 1.69 mg/ml ; 0.0108 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.32 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | 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 |
---|---|---|
With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 0 - 20℃; for 2.0h; | General procedure: To a solution of ester in THF is added DIBAL-H dropwise at 0 °C. After stirring at room temperature for 2 hours, water, 15percent NaOH solution, water, and anhydrous sodium sulfate are added sequentiallly at 0 °C. The resulting slurry is stirred at room temperature for 1 hour and then filtered. The filter cake is washed with EA and the filtrate is concentrated.Following Procedure D using 13 (819 mg, 3.17 mmol), THF (5 mL), DIBAL- H (1.5 M in toluene, 8.4 mL, 12.6 mmol), then quench with water (0.50 mL), 15percent NaOH solution (0.50 mL), water (1.26 mL), and anhydrous sodium sulfate (5 g), and purify with silica gel column chromatography (EA:PE = 1 : 1) to give A17 as a white solid (610 mg, 89percent yield). (MS: [M+H]+ 217.0) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 16.0h; | To a mixture of 113 (1.02 g, 653 mrnoi) and PPh3 (3.4g, 131 mmol)in DCM (50 mL) is added carbon tetrabromide (4.3 g, 13.1 rnrnoi). After stirring at room temperature for 16 hours, the mixture is diluted with DCM, washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (EA:PE 1:20) to give 137 as a pale yellow oil (900 mg, 63percent). (MS: [M÷H] 2190) |
With dibromo sulfoxide; In dichloromethane; at 20℃; for 2.5h; | To a solution of the above compound (0.19 g, 1.2 mmol) in 8.5 mL CH2CI2 was added thionyl bromide (0.1 1 mL, 1.5 mmol). The reaction was stirred at room temperature for 2.5 h and quenched with saturated aqueous ammonium chloride. The layers were separated, and the organic portion was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to afford 5-(bromomethyl)-2-(methylsulfanyl)pyrimidine that gave a mass ion (ES+) of 221.1 (83/4Br) for M+H\\ | |
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 1.0h; | To the solution of <strong>[19858-50-5](2-(methylthio)pyrimidin-5-yl)methanol</strong> (0.88 g, 5.6 mmol) in DCM (20 ml) at 0°C was added triphenylphosphine (2.1 g, 7.9 mmol) and carbon tetrabromide(2.6 g, 7.9 mmol). The resulting solution was stirred at 0°C for 1 hour. The reaction mixture was purified on silica gel column using EtOAc/hexane as eluting solvents to give 5- (bromomethyl)-2-(methylthio)pyrimidine. LC/MS: (M+ 1 ): 218.90; 220.90. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 14N-[(3/^,43/4-3-Hydroxytetrahydro-2H-pyran-4-yl]-4-[2-(methylsulfanyl)pyrimidin-5- yljmethyl } quinoline-2-carboxamideEthyl 4-(4,4,5,5-tetramethyl-l ,3i2-dioxaborolan-2-yl)quinoline-2-cai-boxylate (K4) was prepared as described in Example 11.To a solution of methyl 2-(methylsulfanyl)pyrimidine-5-carboxylate (Nl) (0.23 g, 1.2 mmol) in 20 mL THF at -78 °C was added disobutylaluminum hydride (3.2 mL, 1.0 M solution in toluene). The reaction mixture stirred for 40 min at -78 °C, and then additional disobutylaluminum hydride (5 eq.) was added dropwise. The reaction mixture was stirred for 2 h, and then quenched with concentrated acetic acid. The reaction mixture was warmed to room temperature and filtered to obtain a biphasic solution. The layers were separated, and the organics were dried over sodium sulfate, filtered, and concentrated to afford [2-(methylsuifanyl)pyrimidin-5-yl]methanol (N2) that gave a mass ion (ES+) of 157.1 for M+H+. | ||
With diisobutylaluminium hydride; In toluene; at -78 - 0℃; for 1.0h; | To the solution of methyl 2-(methylthio)pyrimidine-5-carboxylate (3.1 g, 17mmol) in toluene (100 ml) at -78°C was added DIBAL-H (42 ml, 42 mmol) dropwise. Theresulting solution was stirred at -78°C for 30 mm then warmed to 0°C for 30 mm. The reaction was quenched by addition of MeOH (2 mL), sat. Na2504 (50 ml), and iN NaOH (20 mL). The mixture was stirred at RT overnight. After filtration, the filtrate was extracted with EtOAc and DCM. The combined organic phase was dried over Na2504, concentrated and the residue waspurified on silica gel column using EtOAc/hexane as eluting solvents to give (2- (methylthio)pyrimidin-5 -yl)methanol. LC/MS: (M+ 1 ): 156.96. |
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