Ethyl Acetate → HCID 19702786, compound

Reaction equation

C(C1C([C:9]2[N:14]=[C:13]([CH3:15])[C:12]([C:16]([C:18]3[C:19]([CH3:32])=[N:20][C:21](C4C(CC)=NC=NC=4)=[N:22][CH:23]=3)=[O:17])=[CH:11][N:10]=2)=CN=CN=1)C.[BH4-].[Na+].[CH3:35]COC(C)=O>CCO>[CH2:32]([C:19]1[C:18]([CH:16]([C:12]2[C:13]([CH3:15])=[N:14][CH:9]=[N:10][CH:11]=2)[OH:17])=[CH:23][N:22]=[CH:21][N:20]=1)[CH3:35]

Participants

Procedure

To a solution of 63 mg of (4-ethylpyrimidin-5-yl)-4-methylpyrimidin-5-yl ketone in 1 ml EtOH chilled in an ice bath was added 7.4 mg of sodium borohydride. After stirring the solution for 30 minutes, 1 ml of EtOAc was added followed by 1 ml NaH2PO4 (pH=3.0). The mixture was stirred vigorously and the aqueous extracted with EtOAc (3 times). The organic layers were combined, dried (MgSO4) and filtered through silica gel with EtOAc. The solvent was evaporated to yield 52 mg of pure 1-(4-ethylpyrimidin-5-yl)-1-(4-methylpyrimidin-5-yl)methanol.