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Synthesis of 5-(het)aryl- and 4,5-di(het)aryl-2-(thio)morpholinopyrimidines from 2-chloropyrimidine via SN H and cross-coupling reactions

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Abstract

It has been shown that various combinations of nucleophilic aromatic substitution of hydrogen (SN H), SN ipso and the microwave-assisted Suzuki cross-coupling reactions are a versatile method for the synthesis of 5-(het)aryl-2-(thio)morpholinopyrimidine and 4,5-di(het)aryl-2-(thio)morpholinopyrimidine derivatives. All synthesized pyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H37Rv.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. Akademicheskaya/22 ul. S. Kovalevskoy, 620990, Ekaterinburg, Russian Federation

    E. M. Cheprakova, E. V. Verbitskiy, M. A. Ezhikova, M. I. Kodess, M. G. Pervova, P. A. Slepukhin, M. S. Toporova, G. L. Rusinov & V. N. Charushin

  2. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    E. V. Verbitskiy, G. L. Rusinov & V. N. Charushin

  3. Ural Research Institute for Phthisiopulmonology, 50 ul. XXII Parts’ezda, 620039, Ekaterinburg, Russian Federation

    M. A. Kravchenko & I. D. Medvinskiy

Authors
  1. E. M. Cheprakova
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  2. E. V. Verbitskiy
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  3. M. A. Ezhikova
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  4. M. I. Kodess
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  5. M. G. Pervova
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  6. P. A. Slepukhin
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  7. M. S. Toporova
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  8. M. A. Kravchenko
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  9. I. D. Medvinskiy
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  10. G. L. Rusinov
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  11. V. N. Charushin
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Corresponding author

Correspondence to E. V. Verbitskiy.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. N. Chupakhin on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1350–1358, June, 2014.

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Cheprakova, E.M., Verbitskiy, E.V., Ezhikova, M.A. et al. Synthesis of 5-(het)aryl- and 4,5-di(het)aryl-2-(thio)morpholinopyrimidines from 2-chloropyrimidine via SN H and cross-coupling reactions. Russ Chem Bull 63, 1350–1358 (2014). https://doi.org/10.1007/s11172-014-0602-y

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  • DOI: https://doi.org/10.1007/s11172-014-0602-y

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