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Synthesis 2012(1): 120-124  
DOI: 10.1055/s-0031-1289615
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Unusual Regioselective Reactions of 2,4-Bis(methylsulfanyl)pyrimidine under Modified Suzuki and Stille Cross-Coupling Conditions

Abdelbasset A. Farahata,b, David W. Boykin*a
a Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA
Fax: +1(404)4135505; e-Mail: dboykin@gsu.edu;
b Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
Further Information

Publication History

Received 15 September 2011
Publication Date:
22 November 2011 (online)

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Abstract

2,4-Bis(methylsulfanyl)pyrimidine undergoes unusual regioselective cross-coupling reactions with aryl boronic acids and organostannanes in the presence of copper(I) 3-methylsalicylate or copper(I) thiophene-2-carboxylate as a cofactor to give 2-aryl-4-(methylsulfanyl)pyrimidines as the major products. The structures of the products of the coupling reaction were established by X-ray crystallography.

Key words

coupling reactions - cross-coupling - regioselectivity - heterocycles - catalysis - Stille reaction

    References

  • 1a Sun L. Wu J. Zhang L. Luo M. Sun D. Molecules  2011,  16:  5618 
    Search in Google Scholar
  • 1b Barodia SK. Mishra CB. Prakash A. Senthil Kumar JB. Kumari N. Luthra PM. Neurosci. Lett.  2011,  488:  1 
    Search in Google Scholar
  • 1c Beobide G. Castillo O. Cepeda J. Luque A. Pérez-Yáñez S. Román P. Vallejo-Sánchez D. Eur. J. Inorg. Chem.  2011,  68 
  • 1d Baeza A. Mendiola J. Burgos C. Alvarez-Builla J. Vaquero JJ. Eur. J. Org. Chem.  2010,  5607 
  • 1e Prekupec S. Makuc D. Plavec J. Šuman L. Kralj M. Pavelić K. Balzarini J. De Clercq E. Mintas M. Raić-Malić S. J. Med. Chem.  2007,  50:  3037 
    Search in Google Scholar
  • 2 Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Search in Google Scholar
  • 3 Farina V. Krishnamurthy V. Scott WJ. In Organic Reactions   Vol. 50:  Paquette LA. John Wiley; New York: 1997.  p.1 
    Search in Google Scholar
  • 4 Prokopcová H. Kappe CO. Angew. Chem. Int. Ed.  2009,  48:  2276 
    Search in Google Scholar
  • 5a Liebeskind LS. Srogl J. J. Am. Chem. Soc.  2000,  122:  11260 
    Search in Google Scholar
  • 5b Liebeskind LS. Srogl J. Org. Lett.  2002,  4:  979 
    Search in Google Scholar
  • 5c Egi M. Liebeskind LS. Org. Lett.  2003,  5:  801 
    Search in Google Scholar
  • 6a Arroyo IJ. Hu R. Tang BZ. López FI. Peña-Cabrera E. Tetrahedron  2011,  67:  7244 
    Search in Google Scholar
  • 6b Břehová P. Česnek M. Dračínský M. Holý A. Janeba Z. Tetrahedron  2011,  67:  7379 
    Search in Google Scholar
  • 6c Jin W. Du W. Yang Q. Yu H. Chen J. Yu Z. Org. Lett.  2011,  13:  4274 
    Search in Google Scholar
  • 7a Gong Y. Pauls HW. Synlett  2000,  829 
  • 7b Schomaker JM. Delia JJ. J. Org. Chem.  2001,  66:  7125 
    Search in Google Scholar
  • 7c Geneste H. Backfisch G. Braje W. Delzer J. Haupt A. Hutchins CW. King LL. Kling A. Teschendorf H. Unger L. Wernet W. Bioorg. Med. Chem. Lett.  2006,  16:  490 
    Search in Google Scholar
  • 7d Jones NA. Antoon JW. Bowie AL. Borak B. Stevens EP. J. Heterocycl. Chem.  2007,  44:  363 
    Search in Google Scholar
  • 7e Achelle S. Ramondenc Y. Marsais F. Plé N. Eur. J. Org. Chem.  2008,  3129 
  • 7f Anderson SC. Handy ST. Synthesis  2010,  2721 
  • 8 Angiolelli ME. Casalnuovo AL. Selby TS. Synlett  2000,  905 
  • 9a Alphonse F.-A. Suzenet F. Keromnes A. Lebret B. Guillaumet G. Synlett  2002,  447 
  • 9b Alphonse F.-A. Suzenet F. Keromnes A. Lebret B. Guillaumet G. Synthesis  2004,  2893 
  • 9c Alphonse F.-A. Suzenet F. Keromnes A. Lebret B. Guillaumet G. Org. Lett.  2003,  5:  803 
    Search in Google Scholar
  • 10 Itami K. Yamazaki D. Yoshida J. J. Am. Chem. Soc.  2004,  126:  15396 
    Search in Google Scholar
  • 11 Mosrin M. Boudet N. Knochel P. Org. Biomol. Chem.  2008,  6:  3237 
    Search in Google Scholar
  • 12 Sandosham J. Undheim K. Heterocycles  1994,  37:  501 
    Search in Google Scholar
  • 13 Guram AS. Wang X. Bunel EE. Faul MM. Larsen RD. Martinelli MJ. J. Org. Chem.  2007,  72:  5104 
    Search in Google Scholar
  • 16 Sheldrick GM. Acta Crystallogr., Sect. A: Found. Crystallogr.  2008,  64:  112 
    Search in Google Scholar
  • 17 International Tables for X-ray Crystallography   Vol. C:  Wilson AJC. Kynoch Press; Birmingham (UK): 1992.  p.Tables 6.1.1.4 and 4.2.6.8 
14

Bruker APEX 2, SAINT Version 6.45A; Bruker AXS: Madison (WI, USA), 2003.

15

Bruker SAINT V7.68a; Bruker AXS: Madison (WI, USA), 2009.