Acetic Anhydride → N-Acetyl-N-[4-(4-cyano-3,5-difluorophenyl)-6-(ethylamino)-2-pyrimidinyl]acetamide

Participants

Reaction Steps

To a solution of 4-[2-amino-6-(ethylamino)-4-pyrimidinyl]-2,6-difluorobenzaldehyde (1.57 g, 5.64 mmol) in EtOH/water were added sodium carbonate (0.66 g, 6.21 mmol) and hydroxylamine hydrochloride (0.431 g, 6.21 mmol). The resulting mixture was refluxed until the starting material was consumed. The reaction mixture was concentrated to a dark solid. The solid was washed with water and the aqueous washings were extracted with EtOAc. The solid and EtOAc extractions were combined to afford a dark solid. The solid was treated with acetic anhydride (excess) and stirred at 100° C. until the oxime was converted to the nitrile (˜5 days). The reaction mixture was concentrated and co-evaporated with EtOH. The resulting dark solid was triturated with CH3OH to afford the title compound (0.2 g, 10%) as a dark brown solid. LC-MS (ES) m/z=360 [M+H]+.

Provenance & Evidence