Triethylamine → N'-Hydroxy-3-(methylamino)-2-pyrazinecarboximidamide

To a solution of 2-methylamino-3-cyanopyrazine (J. Heterocycl. Chem. 1992, 29, 1689-92) (0.37 g, 2.8 mmol) in methanol (10 mL) was added triethylamine (0.4 mL, 2.8 mmol) followed by hydroxylamine hydrochloride (0.19 g, 2.8 mmol) and the reaction was stirred at room temperature for 4 hours. The mixture was filtered, the filtrate was then evaporated to dryness. The residue was dissolved in ethyl acetate (50 mL) and washed with water (50 mL). The organic layer was dried (MgSO4) and the solvent was removed in vacuo to give the title compound was a white solid (0.45 g).