Dimethyl Sulfoxide → HCID 14086958, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of DMSO (11 g, 138 mmol) in 100 mL of DCM was added Tf2O (42 g, 149 mmol) at −70° C. The resulting mixture was stirred at −70° C. for 15 minutes then a solution of 5-bromopyrazin-2-amine (20 g, 115 mmol, in 100 mL of DCM and 50 mL of DMSO) was added dropwise. The mixture was stirred at −60° C. for 3 hours and diluted with 500 mL of DCM and washed with water. The water layer was basified to pH=11 with aq. Na2CO3 and extracted with DCM twice. The combined DCM layer was washed with brine, dried over Na2SO4 and evaporated to afford 2-bromo-5-[(dimethyl-λ4-sulfanylidene)amino]pyrazine. 1H-NMR (CDCl3, 400 MHz) δ 7.89 (s, 1H), 7.78 (s, 1H), 2.72 (s, 6H).

Provenance & Evidence