Acrylonitrile → Methyl 4-(3-(4-cyano-1-methoxy-1-oxobutan-2-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate

Participants

Reaction Steps

To a solution of methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-methoxy-2-oxoethyl) imidazo[1,5-a]pyrazin-1-yl)benzoate (11.4 g, 23.3 mmol) in THF (100 mL) was added acrylonitrile (1.4 g, 25.6 mmol) and t-BuOK (2.3 mL, 1M in THF). The mixture was stirred at RT for 2 hrs. The reaction was complete detected by TLC (PE/EtOAc 1:1). The mixture was extracted with EA and water, the organic layer was dried and concentrated, the residue was purified by column chromatography on silica gel eluted with PE:EA:DCM=2:1:1 to give methyl 4-(3-(4-cyano-1-methoxy-1-oxobutan-2-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate (12 g, yield 94%).

Provenance & Evidence