Methanol → HCID 118024054, compound
Reaction equation
[CH:1]1([C:7]2[S:19][C:10]3[N:11]=[C:12]([CH3:18])[N:13]=[C:14](/[CH:15]=[CH:16]\[OH:17])[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[BH4-].[Na+]>O>[CH:1]1([C:7]2[S:19][C:10]3[N:11]=[C:12]([CH3:18])[N:13]=[C:14]([CH2:15][CH2:16][OH:17])[C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of (Z)-2-(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)ethenol (430 mg) and MeOH (10 mL) was added NaBH4 (65 mg) in small divided portions, followed by stirring for 15 minutes. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed sequentially with a saturated aqueous NH4Cl solution and brine, and dried over Na2SO4, and the residue was purified by silica gel column (hexane/EtOAc) to obtain 2-(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)ethanol (315 mg).