Dimethylformamide → 3-Azido-2,5-dimethylpyrazine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-chloro-3,5-dimethyl pyrazine (1.0 mL; 8.3 mmol) in dimethylformamide (10 mL) was added sodium azide (539 mg; 8.3 mmol). The reaction was heated to 100° C. and stirred for 12 hours. The reaction was cooled to room temperature, diluted with 50 mL of ethyl acetate and washed with aqueous 10% sodium carbonate (1×50 mL), brine (50 mL), then dried (MgSO4) and filtered. The material was purified using a biotage 12L cartridge eluting with hexanes and ethyl acetate (3:1) to yield an off white solid (42% yield).

Provenance & Evidence