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Russian Chemical Bulletin

, Volume 61, Issue 2, pp 332–342 | Cite as

Synthesis of 4-aminopyrazolo[3,4-d]pyrimidine derivatives from 5-acetyl-6-amino-4-methylsulfanyl- or 5-acetyl-6-amino-4-methylsulfonylpyrimidines

  • A. V. Komkov
  • V. A. Voronkova
  • A. S. Shashkov
  • V. A. Dorokhov
Full Articles

Abstract

Diacetyl ketene N,S-acetal was used for the synthesis of 5-acetyl-6-amino-4-methylsulfanylpyrimidines substituted at the exocyclic nitrogen atom, which were further oxidized with m-chloroperbenzoic acid to the corresponding methylsulfonylpyrimidines. Reactions of hydrazines with these pyrimidines containing vicinal Ac and MeS (or MeSO2) groups were used for the preparation of new 4-aminopyrazolo[3,4-d]pyrimidine derivatives.

Key words

5-acetyl-6-amino-4-methylsulfanylpyrimidines oxidation m-chloroperbenzoic acid 5-acetyl-6-amino-4-methylsulfonylpyrimidines 4-amino-1H-pyrazolo[3,4-d]pyrimid-ines 4-amino-2-phenyl-2H-pyrazolo[3,4-d]pyrimidines hydrazines 

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References

  1. 1.
    S. Schenone, S. Zanoli, C. Brullo, E. Crespan, G. Maga, Curr. Drug Ther., 2008, 3, 158.CrossRefGoogle Scholar
  2. 2.
    P. Traxler, G. Bold, J. Frei, M. Lang, N. Lydon, H. Mett, E. Buchdunger, T. Meyer, M. Mueller, P. Furet, J. Med. Chem., 1997, 40, 3601.CrossRefGoogle Scholar
  3. 3.
    K. J. Curran, J. C. Verheijen, J. Kaplan, D. J. Richard, L. Toral-Barza, I. Hollander, J. Lucas, S. Ayral-Kaloustian, K. Yu, A. Zask, Bioorg. Med. Chem. Lett., 2010, 20, 1440.CrossRefGoogle Scholar
  4. 4.
    Pat. PCT Int. Appl. WO 2009 097446 A1, 2009, Chem. Abstrs, 2009, 151, 221198.Google Scholar
  5. 5.
    Pat. PCT Int. Appl. WO 2006 035061 A1, 2006, Chem. Abstrs, 2006, 144, 370119.Google Scholar
  6. 6.
    Pat. PCT Int. Appl. WO 2005 117909 A2, 2005, Chem. Abstrs, 2006, 144, 51610.Google Scholar
  7. 7.
    Pat. PCT Int. Appl. WO 2005 039506 A2, 2005, Chem. Abstrs, 2005, 142, 447414.Google Scholar
  8. 8.
    Pat. PCT Int. Appl. WO 2008 039359 A2, 2008, Chem. Abstrs, 2008, 148, 426905.Google Scholar
  9. 9.
    Pat. PCT Int. Appl. WO 2008 140947 A1, 2008, Chem. Abstrs, 2008, 149, 576576.Google Scholar
  10. 10.
    D. C. Miller, W. Klute, A. Calabrese, A. D. Brown, Bioorg. Med. Chem. Lett., 2009, 19, 6144.CrossRefGoogle Scholar
  11. 11.
    S. Schenone, O. Bruno, M. Radi, M. Botta, Mini-Rev. Org. Chem., 2009, 6, 220.CrossRefGoogle Scholar
  12. 12.
    H. A. Burch, J. Med. Chem., 1968, 11, 79.CrossRefGoogle Scholar
  13. 13.
    Y. Tominaga, Y. Honkawa, M. Hara, A. Hosomi, J. Heterocycl. Chem., 1990, 27, 775.CrossRefGoogle Scholar
  14. 14.
    Y. Tominaga, Y. Matsuoka, Y. Oniyama, Y. Uchimura, H. Komiya, M. Hirayama, S. Kohra, A. Hosomi, J. Heterocycl. Chem., 1990, 27, 647.CrossRefGoogle Scholar
  15. 15.
    E. I. Al-Afaleg, S. A. Abubshait, Molecules, 2001, 6, 621.CrossRefGoogle Scholar
  16. 16.
    A. M. F. Oliveira-Campos, A. M. Salaheldin, L. M. Rodrigues, ARKIVOC, 2007, XVI, 92.Google Scholar
  17. 17.
    J. Quiroga, J. Trilleras, B. Insuasty, R. Abonia, M. Nogueras, A. Marchal, J. Cobo, Tetrahedron Lett., 2008, 49, 3257.CrossRefGoogle Scholar
  18. 18.
    C. Tumkyavichyus, Khim. Geterotsikl. Soedin., 1996, 831 [Chem. Heterocycl. Compd. (Engl. Transl.), 1996, 32, 716].Google Scholar
  19. 19.
    M. T. Cocco, C. Congiu, V. Onnis, J. Heterocycl. Chem., 2000, 37, 707.CrossRefGoogle Scholar
  20. 20.
    A. V. Komkov, A. M. Sakharov, V. S. Bogdanov, V. A. Dorokhov, Izv. Akad. Nauk, Ser. Khim., 1995, 1324 [Russ. Chem. Bull. (Engl. Transl.), 1995, 44, 1278].Google Scholar
  21. 21.
    V. A. Dorokhov, A. V. Komkov, E. M. Shashkova, V. S. Bogdanov, M. N. Bochkareva, Izv. Akad. Nauk, Ser. Khim., 1993, 1932 [Russ. Chem. Bull. (Engl. Transl.), 1993, 42, 1848].Google Scholar
  22. 22.
    V. A. Dorokhov, M. F. Gordeev, E. M. Shashkova, A. V. Komkov, V. S. Bogdanov, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2600 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1991, 40, 2274].Google Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • A. V. Komkov
    • 1
  • V. A. Voronkova
    • 1
  • A. S. Shashkov
    • 1
  • V. A. Dorokhov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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