Download PDF
Synthesis 2010(4): 689-693  
DOI: 10.1055/s-0029-1218597
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Novel N,3-Substituted 3H-[1,2,3]Triazolo[4,5-d]pyrimidin-5-amines

Finn K. Hansen, Detlef Geffken*
Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany
Fax: +49(40)428386573; e-Mail: geffken@chemie.uni-hamburg.de;
Further Information

Publication History

Received 1 September 2009
Publication Date:
11 December 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Novel N,3-substituted 3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amines were prepared by an expedient method starting from 2-chloro-5-nitropyrimidin-4-yl thiocyanate via N²,N4-substituted 5-nitropyrimidine-2,4-diamines.

Key words

triazolopyrimidines - 5-nitropyrimidine-2,4-diamines - cyclization - hydrogenation - nucleophilic aromatic substitution

    References

  • 1 Kelley JL. Davis RG. McLean EW. Glen RC. Soroko FE. Cooper BR. J. Med. Chem.  1995,  38:  3884 
    CrossrefSearch in Google Scholar
  • 2 Betti L. Biagi G. Giannaccini G. Giorgi I. Livi O. Lucacchini A. Manera C. Scartoni V. J. Med. Chem.  1998,  41:  668 
    CrossrefSearch in Google Scholar
  • 3 Biagi G. Bianucci AM. Coi A. Costa B. Fabbrini L. Giorgi I. Livi O. Micco I. Pacchini F. Santini E. Leonardi M. Nofal FA. Salerni OL. Scartoni V. Bioorg. Med. Chem.  2005,  13:  4679 
    CrossrefSearch in Google Scholar
  • 4a Love CJ, Cooymans LP, and Vandermaesen N. inventors; (Janssen Pharmaceutica N.V., Belgium) Patent WO  2006075023.  ; Chem. Abstr. 2006, 145, 167273
  • 4b Lum C. Kahl J. Kessler L. Kucharski J. Lundstrom J. Miller S. Nakanishi H. Pei Y. Pryor K. Roberts E. Sebo L. Sullivan R. Urban J. Wang Z. Bioorg. Med. Chem. Lett.  2008,  18:  3578 
    Search in Google Scholar
  • 5 Dille KL. Sutherland ML. Christensen BE. J. Org. Chem.  1955,  20:  171 
    CrossrefSearch in Google Scholar
  • 6a Brown DJ. J. Appl. Chem.  1954,  4:  72 
    Search in Google Scholar
  • 6b Brown DJ. J. Appl. Chem.  1957,  7:  109 
    Search in Google Scholar
  • 6c Wiley RH. Lanet J. Hussung KH. J. Heterocycl. Chem.  1964,  1:  175 
    Search in Google Scholar
  • 6d Bacon RGR. Hamilton SD. J. Chem. Soc., Perkin Trans. 1  1974,  1970 
  • 6e Barlin GB. J. Chem. Soc. B  1967,  954 
  • For nucleophilic displacement of the SCN group, see:
  • 7a Takahashi T. Naito T. Inoue S. Chem. Pharm. Bull.  1958,  6:  334 
    Search in Google Scholar
  • 7b Naito T. Inoue S. Chem. Pharm. Bull.  1958,  6:  338 
    Search in Google Scholar
  • 8 Sugiura S. Suzuki E. Naito T. Inoue S. Chem. Pharm. Bull.  1968,  16:  745 
    CrossrefSearch in Google Scholar