Aldehydes and ketones in the presence of a solution of an alkali- or alkaline earth-metal in liquid ammonia, or a suspension of these metals in other solvents, can be used to alkylate the pyrazine ring in moderate to good yields. This alkylation has been successfully applied to pyrazine itself and to alkyl-, dialkyl-, amino- and methoxy-pyrazines. A mechanism for the reaction is proposed.
A. F. Bramwell, L. S. Payne, G. Riezebos, P. Ward and R. D. Wells, J. Chem. Soc. C, 1971, 1627 DOI: 10.1039/J39710001627
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