Tetrabutylammonium Fluoride → 1-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-3-ylmethylamino)pyridin-3-yl)-N-(2-hydroxyethyl)-1H-pyrrole-3-carboxamide

Participants

Reaction Steps

tert-Butyl 3-((5-(3-(2-(tert-butyldimethylsilyloxy)ethylcarbamoyl)-1H-pyrrol-1-yl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (80 mg, 0.118 mmol) was dissolved in THF (2 mL) and tetrabutylammonium fluoride on silica (1.5 mmol/g; 237 mg, 0.355 mmol) was added. The reaction mixture was stirred for 1 h at room temperature. The mixture was filtered and the solvent was evaporated. The residue was dissolved in methanol (1 mL) and absorbed on to a TsOH solid phase extraction cartridge. After 1.5 h the cartridge was eluted with 7M ammonia in methanol. The eluent was evaporated to dryness and the residue was purified by HPLC to give 1-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-3-ylmethylamino)pyridin-3-yl)-N-(2-hydroxyethyl)-1H-pyrrole-3-carboxamide.

Provenance & Evidence