Sodium borohydride → HCID 68644536, compound

Participants

Reaction Steps

Sodium borohydride (2.6 g, 69 mmol) was added to a solution of 4-[5-(4-cyano-benzyloxy)-6-methyl-2-oxo-4H-pyrido[3,4-d][1,3]oxazin-1 ylmethyl]-benzonitrile (83) (587 mg, 1.4 mmol) in a mixture of methyl alcohol and dichloromethane (1:1, 20 mL) at 0° C. The resulting solution was warmed to room temperature and stirred for 24 hours. The solvent was evaporated, residue was diluted with water and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated. The product was purified by column chromatography on silica gel using a gradient mixture of dichloromethane:methyl alcohol (1:0 to 40:1) as eluant to give 4-{[4-hydroxymethyl-6-methyl-5-(4-cyano-benzyloxy)-pyridin-3-ylamino]-methyl}-benzonitrile (87) (175 mg, 32% yield) as a colorless solid.

Provenance & Evidence