Sodium Cyanide → 3-Amino-6-bromopyrazine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of copper(i) cyanide (1.20 g, 13.42 mmol) and sodium cyanide (0.658 g, 13.42 mmol) in DMF (10 mL) was heated to 125° C. 2-amino-3,5-dibromo pyrazine (2.61 g, 10.32 mmol) was added in portions. The reaction was stirred at 125° C., and after 5 h quenched in ice cold NaHCO3 solution. The black precipitate was filtrated off and the filtrate was extracted (3×) with EtOAc. The organic layer was washed with brine, dried and evaporated. Purification by chromatography (CH2Cl2) gave pure 3-amino-6-bromopyrazine-2-carbonitrile 14 (1.38 g, 67.2%). 1H-NMR (400 MHz, CDCl3) 5.29 (br s, 2H), 8.30 (s, 1H). (m/z)=199 and 201 (M+H)+.

Provenance & Evidence