Synthesis 2005(7): 1164-1168  
DOI: 10.1055/s-2005-861811
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of Pyrrolo[2,3-d]pyrimidine Derivatives by Amine Oxide Rearrangement

Krishna C. Majumdar*, Anindita Biswas, Partha P. Mukhopadhyay
Department of Chemistry, University of Kalyani, Kalyani 741 235,West Bengal, India
Fax: +91(33)25828282; e-Mail: kcm@klyuniv.ernet.in;
Further Information

Publication History

Received 6 September 2004
Publication Date:
29 March 2005 (eFirst)

Abstract

Regioselective synthesis of biologically important pyrrolo[2,3-d]pyrimidine derivatives 4a-h in 75-82% yields are reported. The applied conditions of the less studied rearrangement are the oxidation of 6-N-(4-aryloxybut-2-yn-1-yl)-N-methyl(or ethyl)amino-1,3-dimethyluracils 3a-h with m-chloroperoxybenzoic acid at 0-5 °C for one hour and then stirring at room temperature for 10-12 hours. Compounds 3a-h are prepared by the reaction of 1,3-di­methyl-6-chlorouracil (1) with different (4-aryloxybut-2-yn-1-yl)-N-methylamines or (4-aryloxybut-2-yn-1-yl)-N-ethylamines 2 in refluxing ethanol for 12-14 hours.

    References

  • 1 Gupta PK. Daunert S. Nassiri MR. Wotring LL. Drach JC. Townsend LB. J. Med. Chem.  1989,  32:  402 
  • 2 Gupta PK. Nassiri MR. Coleman LA. Wotring LL. Drach JC. Townsend LB. J. Med. Chem.  1989,  32:  1420 
  • 3 Bhattacharya BK. Ojwang JO. Rando RF. Huffman JH. Revankar GR. J. Med. Chem.  1995,  38:  3957 
  • 4 Chin JE. Hatfield CA. Winterrowd GE. Krzesicki RF. Shull KL. Fidler SF. Kolbasa KP. Brashler JR. Griffin RL. Fleming WE. Justen JM. Banitt LS. Bundy GL. Richards IM. J. Pharm. Exp. Ther.  1999,  290:  188 
  • 5 Miyasaka T. Tanaka H. Baba M. Hayakawa H. Walker RT. Balzarini J. DeClercq E. J. Med. Chem.  1989,  32:  2507 
  • 6 Baba M. Tanaka H. DeClercq E. Pauwels R. Balzarini J. Schols D. Nakashima H. Perno CF. Walker RT. Miyasaka T. Biochem. Biophys. Res. Commun.  1989,  165:  1375 
  • 7 DeClercq E. Med. Res. Rev.  1993,  13:  229 
  • 8a Gallo RC. Sci. Am.  1986,  255:  78 
  • 8b Gallo RC. Sci. Am.  1987,  256:  38 
  • 9a Heidelberger C. Pyrimidine and Pyrimidine Antimetabolites in Cancer Medicine   Holland JF. Frei E. Lea and Febiger; Philadelphia: 1984.  p.801 
  • 9b Taylor EC. Liu B. J. Org. Chem.  2003,  68:  9938 
  • 10 DeClercq E. Descamps J. Somer PD. Barr PJ. Jones AS. Walker RT. Proc. Natl. Acad. Sci. USA  1979,  76:  2947 
  • 11 Heidelberger C. King DH. In Antiviral Agents in Pharmacology and Therapeutics   Vol. 6:  Shugar D. Pergamon; Oxford: 1979.  p.427 
  • 12 Mitsuya H. Weinhold KJ. Furman PA. St. Clair MH. Lehrman SN. Gallo RC. Bolognesi D. Barry DW. Broder S. Proc. Natl. Acad. Sci. U.S.A.  1985,  82:  7096 
  • 13 Fischl MA. Richman DD. Grieco MH. Gottlieb MS. Volberdin PA. Laskin OL. Leedom JM. Groopman JE. Mildvan D. Schooley RT. Jackson GG. Durack DT. King D. N. Engl. J. Med.  1987,  317:  185 
  • 14 Griengl H. Bodenteich M. Hayden W. Wanek E. Streicher W. Stutz P. Bachmayer H. Ghazzouli I. Rosenwirth B. J. Med. Chem.  1985,  28:  1679 
  • 15 Macilwain C. Nature  1993,  365:  378 
  • 16a Kundu NG. Das P. J. Chem. Soc., Chem. Commun.  1995,  99 
  • 16b Botta M. Saladino R. Lamba D. Nicoletti R. Tetrahedron  1993,  49:  6053 
  • 17a Majumdar KC. Mukhopadhyay PP. Synthesis  2003,  920 
  • 17b Majumdar KC. Das U. Jana NK. J. Org. Chem.  1998,  63:  3550 
  • 17c Majumdar KC. Basu PK. Mukhopadhyay PP. Sarkar S. Ghosh SK. Biswas P. Tetrahedron  2003,  59:  2151 
  • 18a Majumdar KC. Sarkar S. Bhattacharrya T. Tetrahedron  2003,  59:  4309 
  • 18b Majumdar KC. Bhattacharrya T. Synthesis  2001,  4309 
  • 18c Majumdar KC. Mukhopadhyay PP. Synthesis  2004,  1864 
  • 19a Hillard JB. Reddy KV. Majumdar KC. Thyagarajan BS. Tetrahedron Lett.  1974,  1999 
  • 19b Hillard JB. Reddy KV. Majumdar KC. Thyagarajan BS. J. Heterocycl. Chem.  1974,  11:  369 
  • 19c Thyagarajan BS. Majumdar KC. J. Heterocycl. Chem.  1975,  12:  43 
  • 20a Majumdar KC. Chattopadhyay SK. J. Chem. Soc., Chem. Commun.  1987,  524 
  • 20b Majumdar KC. Chattopadhyay SK. Khan AT. J. Chem. Soc., Perkin Trans. 1  1989,  1285 
  • 20c Majumdar KC. Ghosh SK. J. Chem. Soc., Perkin Trans. 1  1994,  2889 
  • 21a Majumdar KC. Jana GH. Das U. J. Chem. Soc., Chem. Commun.  1997,  517 
  • 21b Majumdar KC. Jana GH. Das U. J. Chem. Soc., Perkin Trans. 1  1997,  1229 
  • 21c Majumdar KC. Samanta SK. Tetrahedron Lett.  2002,  43:  2119 
  • 22 Majumdar KC. Kundu UK. Ghosh S. Tetrahedron  2002,  58:  10309