Sodium cyanoborohydride → 4-(3-Chlorophenyl)-1,2-dihydroimidazo[1,5-a]pyrimidine-8-carboxamide

Participants

Reaction Steps

To a solution of 5.39 g of 4-(m-chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide (Example 14) in 100 ml of glacial acetic acid, was added in portions 2.8 g of sodium cyanoborohydride at room temperature under nitrogen. The mixture was stirred at room temperature for 2 hours. The solvent was evaporated in vacuo to give an oil, and this was dissolved in dichloromethane, then washed with saturated sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and filtered through a short column of hydrous magnesium silicate. Evaporation of the solvent gave a yellow solid which was recrystallized from acetonitrile to give 3.25 g of the desired product as a yellow solid, mp 182°-184° C.

Provenance & Evidence