Synthesis of amino derivatives of triazolopyrimidine

Article abstract of DOI:10.1134/S1070428006090272

Heterocyclization of 1-(4,6-dimethylpyrimidin-2-yl)-4-R-thiosemicarbazides by the action of methyl iodide in ethanol in the presence of sodium acetate is accompanied by Dimroth rearrangement leading to the formation of 5,7-dimethyl-2-R-amino[1,2,4]triazolo[1,5-a]pyrimidines. Analogous heterocyclization of 4-aryl-1-(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl) thiosemicarbazides gives 3-arylamino-7-methyl-5-oxo-[1,2,4]triazolo[4,3-a] pyrimidines. The presence in the pyrimidine ring of a carbonyl group capable of forming hydrogen bond with protons of the amino group stabilizes the molecule, thus hampering the Dimroth rearrangement.

Full text of DOI:10.1134/S1070428006090272

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