Advertisement

Russian Chemical Bulletin

, Volume 63, Issue 6, pp 1350–1358 | Cite as

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

  • E. M. Cheprakova
  • E. V. Verbitskiy
  • M. A. Ezhikova
  • M. I. Kodess
  • M. G. Pervova
  • P. A. Slepukhin
  • M. S. Toporova
  • M. A. Kravchenko
  • I. D. Medvinskiy
  • G. L. Rusinov
  • V. N. Charushin
Full Articles

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.

Key words

pyrimidines morpholine thiomorpholine cross-coupling microwave irradiation nucleophilic aromatic substitution of hydrogen antituberculosis activity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    G. W. Rewcastle Comprehensive Heterocyclic Chemistry III, Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Elsevier, Oxford, 2008, Vol. 8.02, p. 117.CrossRefGoogle Scholar
  2. 2.
    WO Pat. 047284; Chem. Abstr., 2005, 142, 482057.Google Scholar
  3. 3.
    WO Pat. 172043; Chem. Abstr., 2012, 158, 104901.Google Scholar
  4. 4.
    WO Pat. 100438; Chem. Abstr., 2009, 151, 272907.Google Scholar
  5. 5.
    WO Pat. 109605; Chem. Abstr., 2009, 151, 328872.Google Scholar
  6. 6.
    WO Pat. 055942; Chem. Abstr., 2012, 156, 613424.Google Scholar
  7. 7.
    E. V. Verbitskiy, E. M. Cheprakova, P. A. Slepukhin, M. I. Kodess, M. A. Ezhikova, M. G. Pervova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Tetrahedron, 2012, 68, 5445.CrossRefGoogle Scholar
  8. 8.
    E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, O. N. Chupakhin, E. M. Cheprakova, P. A. Slepukhin, M. G. Pervova, M. A. Ezhikova, M. I. Kodess, Eur. J. Org. Chem., 2012, 33, 6612.Google Scholar
  9. 9.
    F. L. Tietze, T. Eicher, Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschunglaboratorium, Georg Thieme Verlag, Stuttgart-New York, 1991.CrossRefGoogle Scholar
  10. 10.
    G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112.CrossRefGoogle Scholar
  11. 11.
    V. N. Vasilev, Micobacteriozy i mikozy legkikh [Mycobacterioses and pulmonary mycosis], Meditsina i Fizkultura, Sofia, 1971, 382 pp. (in Russian).Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • E. M. Cheprakova
    • 1
  • E. V. Verbitskiy
    • 1
    • 2
  • M. A. Ezhikova
    • 1
  • M. I. Kodess
    • 1
  • M. G. Pervova
    • 1
  • P. A. Slepukhin
    • 1
  • M. S. Toporova
    • 1
  • M. A. Kravchenko
    • 3
  • I. D. Medvinskiy
    • 3
  • G. L. Rusinov
    • 1
    • 2
  • V. N. Charushin
    • 1
    • 2
  1. 1.I. Ya. Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesEkaterinburgRussian Federation
  2. 2.Ural Federal University named after the First President of Russia B. N. YeltsinEkaterinburgRussian Federation
  3. 3.Ural Research Institute for PhthisiopulmonologyEkaterinburgRussian Federation

Personalised recommendations