Pyridine → 8-Chloro-3-(3-methyloxetan-3-yl)imidazo[1,5-a]pyrazine

Participants

Reaction Steps

To a stirred solution of N-((3-chloropyrazin-2-yl)methyl)-3-methyloxetane-3-carboxamide (1.945 mmol, 0.47 g) in dichloromethane (10 ml) cooled in an ice-bath was added pyridine (27.2 mmol, 2.198 ml) and trifluoromethane sulfonic anhydride (11.67 mmol, 1.971 ml). The ice-bath was removed and the reaction was stirred at room temperature. After 2 hours the reaction mixture was cooled in ice-bath, diluted with ethyl acetate (5 mL) and quenched with aqueous sodium hydrogencarbonate. The organic layer separated and the aqueous layer washed four times with ethyl acetate. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo. Purification by column chromatography (silica gel, ethyl acetate) yielded 8-chloro-3-(3-methyloxetan-3-yl)imidazo[1,5-a]pyrazine (0.56 g).

Provenance & Evidence