Ammonia → 3-[1-(Cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,7-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-e][1,2,4]triazin-6-one

Participants

Reaction Steps

5 ml (53.642 mmol) of phosphoryl chloride were added to 376 mg (0.863 mmol) of methyl 2-{3-[1-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-hydroxy-1,2,4-triazin-6-yl}-2-methylpropanoate, and the mixture was stirred at RT overnight. The reaction solution was diluted with 20 ml of dry acetonitrile and, with ice-cooling, slowly added dropwise to 83 ml of a 25% strength aqueous ammonia solution, and the mixture was stirred at RT overnight. The reaction mixture was concentrated on a rotary evaporator and the precipitate was filtered off. The residue was triturated with DMF/methanol, filtered off with suction and dried under high vacuum. This gave 84 mg of the target compound (24% of theory).

Provenance & Evidence