Hydrochloric Acid → 4-Chloro-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine

Participants

Reaction Steps

A solution of triethylamine (29.1 ml) in dichloromethane (100 ml) was added to a mixture composed of 1-(2-amino-4,6-dichloropyrimidin-5-yl)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethan-1-one (16 g), (4-methoxybenzyl)-hydrazine hydrochloride (14.1 g) and dichloromethane (400 ml) under cooling in an ice bath over 15 minutes. After stirring under cooling in an ice bath for 1.5 hours, a 0.2 N hydrochloric acid solution (1000 ml) was added to the reaction mixture, followed by extraction with dichloromethane (400 ml). The organic layer was washed with brine (500 ml) and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-chloroform) to obtain the title compound (16.5 g, 78%) as a solid.

Provenance & Evidence