Ammonium Chloride → Thieno[2,3-d]pyrimidine-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

LiAlH4 (1M in THF, 0.26 mL) was added dropwise to N-methoxy-N-methylthieno[2,3-d]pyrimidine-6-carboxamide (intermediate 12) (117 mg) in THF (6 mL) at −78° C. under an inert atmosphere. The reaction was allowed to stir at −78° C. for 30 minutes and then allowed to warm to 0° C. Saturated aqueous-ammonium chloride (2 mL) was added and allowed to stir at 0° C. for 10 minutes. The organic layer was separated and the aqueous layer extracted with diethyl ether (2×15 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with hexane:EtOAc (1:4) afforded the title compound as a white solid (60 mg, 70%);

Provenance & Evidence