Methanol → 2-Amino-5-chloro-3-methoxypyrazine

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Reaction Steps

Sodium (2.82 g) was dissolved in dry methanol (50 ml) under argon and 2-amino-3-bromo-5-chloropyrazine (1.68 g) was added in small portions at ambient temperature with stirring. The resulting stirred solution was heated under reflux and an argon atmosphere for 4 hours. Water (10 ml) was added at ambient temperature and the solvent removed by evaporation. A further volume of water (10 ml) was added and the aqeous phase was extracted with dichloromethane (3×50 ml). Combined organic extracts were dried (MgSO4) and evaporated to give 2-amino-5-chloro-3-methoxypyrazine (1.28 g), m.p. 102°-103° C.; 1H NMR (d6DMSO): 3.90 (s, 3H), 7.53 (s, 1H); mass spectrum (+ve CI): 160 (M+H)+.

Provenance & Evidence