Sodium borohydride → (2-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol
Reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH:11]=[O:12])=[C:8]([CH3:13])[C:6]=2[N:7]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][OH:12])=[C:8]([CH3:13])[C:6]=2[N:7]=1Participants
4
Procedure
To a suspension of 2-chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (400 mg, 1.34 mmol) in methanol at 0° C. was added sodium borohydride and. After stirring for 2 hours, the mixture was quenched with 50:50 H2O:NaHCO3(sat. aq). The methanol was removed under reduced pressure to give a suspension which was filtered and washed with H2O followed by ether to give (2-chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-methanol.