Download PDF
Synthesis 2006(8): 1343-1350  
DOI: 10.1055/s-2006-926414
PAPER
© Georg Thieme Verlag Stuttgart · New York

Suzuki Coupling at the 2-Position of Densely Functionalized Pyrimidones

Stefania Colarusso*, Mélina Girardin, Immacolata Conte, Frank Narjes
IRBM-Merck Research Laboratories Rome, Via Pontina km 30.600, Pomezia 00040, Rome, Italy
Fax: +39(069)1093654; e-Mail: stefania_colarusso@merck.com;
Further Information

Publication History

Received 23 November 2005
Publication Date:
28 March 2006 (online)

    Permissions and Reprints All articles of this category

Abstract

A variety of ethyl 1-substituted 2-aryl-5-ethoxy-6-oxo-1,6-dihydropyrimidine-4-carboxylates were synthesized by efficient thermal or microwave-promoted Suzuki coupling of 2-chloro-N1-substituted precursors.

Key words

antiviral agents - pyrimidones - cross-coupling

    References

  • 1 Summa V. Petrocchi A. Matassa VG. Taliani M. Laufer R. De Francesco R. Pace P. J. Med. Chem.  2004,  47:  5336 
    CrossrefPubMedGoogle Scholar
  • 2 Stansfield I. Avolio S. Colarusso S. Gennari N. Narjes F. Pacini B. Ponzi S. Harper S. Bioorg. Med. Chem. Lett.  2004,  14:  5085 
    CrossrefGoogle Scholar
  • 3a Gong Y. Pauls HW. Synlett  2000,  829 
    CrossrefGoogle Scholar
  • 3b Cocuzza AJ. Chideste DR. Culp S. Fitzgerald L. Gilligan P. Bioorg. Med. Chem. Lett.  1999,  9:  1063 
    CrossrefGoogle Scholar
  • 4 Zhang D. Sham K. Cao G.-q. Hungate R. Dominguez C. Tetrahedron Lett.  2002,  43:  8901 
    CrossrefGoogle Scholar
  • 5 Wierenga W. Nicholas JA. In Comprehensive Medicinal Chemistry   Vol. 3:  Pergamon; London: 1990.  p.1122-1124  
    Google Scholar
  • 6 Ivin BA. Rutkovskii GV. Rusavskaya TN. Smorygo NA. Sochilin EG. Khim. Get. Soed.  1974,  11:  1527 ; Chem. Abstr. 1975, 82, 57638
    Google Scholar
  • 7 Wu WX. inventors; US Patent  5925764.  ; Chem. Abstr. 1999, 131, 87822
  • 8a Littke AF. Fu GC. Angew. Chem. Int. Ed.  1998,  37:  3387 
    Google Scholar
  • 8b Littke AF. Dai C. Fu GC. J. Am. Chem. Soc.  2000,  122:  4020 
    Google Scholar
  • 8c For an excellent review on Pd-catalyzed cross-coupling of aryl chlorides, see: Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Google Scholar
  • 9 Netherton MR. Fu GC. Org. Lett.  2001,  3:  4295 
    CrossrefPubMedGoogle Scholar
  • 10 Lindström P. Tierney J. Wathey B. Westman J. Tetrahedron  2001,  57:  9225 
    CrossrefGoogle Scholar
  • 11 For a recent and comprehensive review on controlled microwave heating in modern organic synthesis, see: Kappe OC. Angew. Chem. Int. Ed.  2004,  43:  6250 
    CrossrefPubMedGoogle Scholar
  • 12 Walker SD. Barder TE. Martinelli JR. Buchwald SL. Angew. Chem. Int. Ed.  2004,  43:  1871 
    CrossrefGoogle Scholar