Synlett 2012; 23(9): 1305-1308
DOI: 10.1055/s-0031-1290826
letter
© Georg Thieme Verlag Stuttgart · New York

A General Regioselective Synthesis of 2,4-Diarylpyrimidines from 2- Thiouracil through Two Orthogonal Cross-Coupling Reactions

Miroslava Čerňová
a   Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12843 Prague 2, Czech Republic
b   Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, 16610 Prague 6, Czech Republic, Fax: +420(220)183559   Email: hocek@uochb.cas.cz
,
Radek Pohl
b   Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, 16610 Prague 6, Czech Republic, Fax: +420(220)183559   Email: hocek@uochb.cas.cz
,
Blanka Klepetářová
b   Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, 16610 Prague 6, Czech Republic, Fax: +420(220)183559   Email: hocek@uochb.cas.cz
,
Michal Hocek*
a   Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12843 Prague 2, Czech Republic
b   Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, 16610 Prague 6, Czech Republic, Fax: +420(220)183559   Email: hocek@uochb.cas.cz
› Author Affiliations
Further Information

Publication History

Received: 21 February 2012

Accepted after revision: 08 March 2012

Publication Date:
07 May 2012 (online)


Abstract

A novel efficient synthesis of 2,4-diarylpyrimidines was developed based on phosphonium-mediated Suzuki coupling of 2-(methylsulfanyl)pyrimidin-4(3H)-one (at position 4) followed by the Liebeskind–Srogl cross-coupling (at position 2) under microwave irradiation.

Supporting Information

 
  • References

    • Examples:

    • 1a Yaziji V, Rodríguez D, Gutiérrez-de-Terán G, Coelho A, Caamano O, García-Mera X, Brea J, Loza MI, Cadavid MI, Sotelo E. J. Med. Chem. 2011; 54: 457
    • 1b Large JM, Torr JE, Raynaud FI, Clarke PA, Hayes A, Stefano F, Urban F, Shuttleworth SJ, Saghir N, Sheldrake P, Workman P, McDonald E. Bioorg. Med. Chem. 2011; 19: 836
    • 1c Guay D, Beaulieu Ch, Belley M, Crane SN, DeLuca J, Gareau Y, Hamel M, Henault M, Hyjazie H, Kargman S, Chan CC, Xu L, Gordon R, Li L, Mamane Y, Morin N, Mancini J, Thérien M, Tranmer G, Truong VL, Wang Z, Black WC. Bioorg. Med. Chem. Lett. 2011; 21: 2832
    • 1d Erdmann F, Weiwad M, Kilka S, Karanik M, Patzel M, Baumgrass R, Liebscher J, Fischer G. J. Biol. Chem. 2010; 285: 1888
    • 1e Veldhoven JP. D, Chang LC. W, Kunzel JK. F. D, Mulder-Krieger T, Struensee-Link R, Beukers MW, Brussee J, Ijzerman AP. Bioorg. Med. Chem. 2008; 16: 2741
    • 2a Yan S, Tang Y, Yu F, Lin J. Helv. Chim. Acta 2011; 94: 487
    • 2b Lin M, Chen Q.-Z, Zhu Y, Chen X.-L, Cai J.-J, Pan Y.-M, Zhan Z.-P. Synlett 2011; 1179
    • 2c Bagley MC, Lin Z, Pope SJ. A. Tetrahedron Lett. 2009; 50: 6818
  • 4 Ceide SC, Montalban AG. Tetrahedron Lett. 2006; 47: 4415
  • 5 Farahat AA, Boykin DW. Synthesis 2012; 44: 120
    • Review:

    • 7a Prokopcová H, Kappe CO. Angew. Chem. Int. Ed. 2009; 48: 2276
    • 7b Original paper: Liebeskind LS, Srogl J. Org. Lett. 2002; 4: 979
    • 8a Kusturin C, Liebeskind LS, Rahman H, Sample K, Schweitzer B, Srogl J, Neumann WL. Org. Lett. 2003; 5: 4349
    • 8b Singh BK, Mehta VP, Parmar VS, Van der Eycken E. Org. Biomol. Chem. 2007; 5: 2962
  • 9 Mehta VP, Modha S, Van der Eycken E. J. Org. Chem. 2010; 75: 976
  • 10 Arshad N, Hashim J, Kappe CO. J. Org. Chem. 2009; 74: 5118
  • 11 Barrett HW, Goodman I, Dittmer K. J. Am. Chem. Soc. 1948; 70: 1753
  • 12 Sun Q, Suzenet F, Guillaumet G. J. Org. Chem. 2010; 75: 3473
  • 13 CCDC 863152 (5ab) and CCDC 863153 (5cc) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
    • 14a Bibby MC. Drugs Future 2002; 27: 475
    • 14b Tron GC, Piralli T, Sorba G, Pagliai F, Busacca S, Genazzani AA. J. Med. Chem. 2006; 49: 3033
    • Examples:

    • 15a Bonezzi K, Taraboletti G, Borsotti P, Bellina F, Rossi R, Giavazzi R. J. Med. Chem. 2009; 52: 7906
    • 15b Theeramungkong S, Caldarelli A, Mussarotti A, Aprile S, Caprioglio D, Zaninetti R, Teruggi A, Piralli T, Grosa G, Tron GC, Genazzi AA. J. Med. Chem. 2011; 54: 4977
    • Reviews:

    • 16a Schöter S, Stock C, Bach T. Tetrahedron 2005; 61: 2245
    • 16b Fairlamb IJ. S. Chem. Soc. Rev. 2007; 36: 1036
    • 16c Examples: Hocek M, Pohl R. Synthesis 2004; 2869
    • 16d See also: Kubelka T, Slavětínská L, Klepetářová B, Hocek M. Eur. J. Org. Chem. 2010; 2666
  • 17 Fürstner A, Leitner A, Méndez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13856
  • 18 Yan S, Tang Y, Yu F, Lin J. Helv. Chim. Acta 2011; 94: 487