Potassium Cyanide → 5-Amino-3-chloropyrazine-2-carbonitrile

Participants

Reaction Steps

A mixture of 5-bromo-6-chloropyrazin-2-amine (1.00 g, 4.8 mmol), copper (I) iodide (914 mg, 4.8 mmol), 18-crown-6 (95 mg, 0.36 mmol) and tetrakis(triphenylphosphine)palladium (0) (83 mg, 0.072 mmol) was suspended in dry DMF (20 mL) and a stream of nitrogen was passed through it for 5 minutes. Potassium cyanide (312 mg, 4.8 mmol) was added and the mixture was stirred at room temperature for 30 minutes, then refluxed at 200° C. for 3 hours. The mixture was cooled and diluted with EtOAc and absorbed onto silica gel (10 g). DMF was removed by evaporation in a Genevac evaporator. The product was purified by flash chromatography, eluting with 1:1 ethyl acetate-hexane, to yield the title compound as a yellow solid (607 mg, 3.93 mmol, 82%). 1H NMR (d6-DMSO, 400 MHz) δ 8.1 (br s, 2H), 7.87 (s, 1H). LC-MS (1) Rt=1.20 min; m/z (ESI−) 153 (M−H).

Provenance & Evidence