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Synthesis of amino derivatives of triazolopyrimidine

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Abstract

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.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02094, Ukraine

    R. I. Vas’kevich, P. V. Savitskii, Yu. L. Zborovskii, V. I. Staninets, E. B. Rusanov & A. N. Chernega

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  1. R. I. Vas’kevich
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  2. P. V. Savitskii
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  3. Yu. L. Zborovskii
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  4. V. I. Staninets
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  5. E. B. Rusanov
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  6. A. N. Chernega
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Original Russian Text © R.I. Vas’kevich, P.V. Savitskii, Yu.L. Zborovskii, V.I. Staninets, E.B. Rusanov, A.N. Chernega, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 9, pp. 1417–1422.

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Vas’kevich, R.I., Savitskii, P.V., Zborovskii, Y.L. et al. Synthesis of amino derivatives of triazolopyrimidine. Russ J Org Chem 42, 1403–1408 (2006). https://doi.org/10.1134/S1070428006090272

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  • DOI: https://doi.org/10.1134/S1070428006090272

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