Ammonia → 3-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazine-5,6-diamine

Participants

Reaction Steps

3.602 g (10.677 mmol) of 6-amino-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazin-5-ol in 45 ml of thionyl chloride were added and heated under reflux for 3 h. The reaction mixture was diluted with 200 ml of dry acetonitrile and, with ice-cooling, added dropwise to 500 ml of concentrated aqueous ammonia solution (35% strength). The mixture was stirred at RT overnight. The acetonitrile was removed on a rotary evaporator and the precipitate was filtered off with suction. This gave 3.541 g (purity 67%, 66% of theory) of the target compound. A small amount was purified by preparative HPLC (mobile phase: acetonitrile/water with 0.1% TFA, gradient 30:70→95:5).

Provenance & Evidence