Abstract
The rearrangement of 1-alkyl-2-(carbamoylmethyl)pyrimidinium iodides into substituted 2-alkylaminonicotinamides occurring in alcoholic solutions of amines has been studied. It was shown that in the presence of water the rearrangement of 2-(carbamoylmethyl)-1,4,6-trimethylpyrimidinium iodide is accompanied by the formation of a derivative of 2-oxo-1,2-dihydronicotinic acid, and under the action of ethylamine a “rearrangement and transamination” occurs leading to 2-ethylamino-4,6-dimethylnicotinamide.
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Danagulyan, G.G., Sahakyan, L.G. The Kost-Sagitullin Rearrangement in a Series of 1-Alkyl-2-(carbamoylmethyl)-4,6-dimethylpyrimidinium Iodides. Chemistry of Heterocyclic Compounds 40, 320–325 (2004). https://doi.org/10.1023/B:COHC.0000028628.69948.b6
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DOI: https://doi.org/10.1023/B:COHC.0000028628.69948.b6