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2-Methylsulfanyl-6-Polyfluoroalkyl-Pyrimidin-4-Ones: Synthesis and Nucleophilic Substitution Reactions

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Chemistry of Heterocyclic Compounds Aims and scope

We have optimized the reaction conditions for the synthesis of 2-methylsulfanyl-6-polyfluoro-alkylpyrimidin-4-ones. In particular the yield of trifluoromethyl-substituted heterocycle was increased to 96%, and new polyfluoroalkyl-substituted analogs were prepared. The interaction of these heterocycles with morpholine or hydrazine was shown to result in nucleophilic substitution of the methylsulfanyl group, leading to 2-morpholino- and 2-hydrazino-6-polyfluoroalkylpyrimidin-4-ones. The reaction of 2-(2-phenylhydrazino)-6-trifluoromethylpyrimidin-4-one with paraform produced 5-oxo-2-phenyl-7-tri-fluoromethyl-5H-1,2,4-triazolo[4,3-а]pyrimidin-1-id-2-ium. The lactam structure of the synthesized heterocycles was established by X-ray structural analysis, as well as by IR and NMR spectroscopy.

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The work was performed with financial support from the Russian Foundation for Basic Research (grant 13-03-00617) and the Grants Council of the President of the Russian Federation (grant NSh-3656.2014.3).

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Authors and Affiliations

  1. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoi St. / 20 Akademicheskaya St., Yekaterinburg, 620990, Russia

    O. G. Khudina, Ya. V. Burgart & V. I. Saloutin

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  1. O. G. Khudina
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  2. Ya. V. Burgart
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  3. V. I. Saloutin
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Correspondence to Ya. V. Burgart.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 928-935, June, 2014.

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Khudina, O.G., Burgart, Y.V. & Saloutin, V.I. 2-Methylsulfanyl-6-Polyfluoroalkyl-Pyrimidin-4-Ones: Synthesis and Nucleophilic Substitution Reactions. Chem Heterocycl Comp 50, 856–863 (2014). https://doi.org/10.1007/s10593-014-1539-7

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