Potassium Cyanide → 5-Aminopyrazine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

5-Bromo-pyrazin-2-ylamine was combined with copper (I) iodide (1.3 g, 6.9 mmol), potassium cyanide (0.44 g, 6.8 mmol), tetrakis (triphenylphosphine)palladium(0) (0.95 g, 0.83 mmol), and 18-crown-6 (0.058 g, 0.22 mmol) in DMF (15 mL). The resulting mixture was stirred for 40 min, then heated at reflux (155° C.) for 2 h. The reaction was cooled to room temperature, then allowed to stand overnight. The precipitate was separated by filtration and the filtrate was concentrated to dryness in vacuo. The orange-colored residue was taken up in EtOAc and hexanes and an initial precipitate was formed, then separated by filtration. Upon standing, additional precipitate formed in the mother liquor and was collected by filtration. The solids were combined to yield 0.10 g of a bright orange solid.

Provenance & Evidence