HSAB-driven chemoselective N1-alkylation of pyrimidine bases and their 4-methoxy- or 4-acetylamino-derivatives

Tetrahedron

Volumn 62, Issue 29, 2006, Pages 6848-6854

  Gambacorta, Augusto ^a   Tofani, Daniela ^a   Loreto, Maria Antonietta ^b   Gasperi, Tecla ^b   Bernini, Roberta ^c  

^a ROMA TRE UNIVERSITY   (Italy)

^b CNR Consiglio Nazionale delle Ricerche   (Italy)

^c UNIVERSITY OF TUSCIA   (Italy)

Author keywords

Alkylation; HSAB principle; Pyrimidinones; Regioselection

Indexed keywords

1 ETHYL 4 METHOXY 2(1H) PYRIMIDINONE; 1 ETHYL 4 METHOXY 5 METHYL 2(1H) PYRIMIDINONE; 1 ETHYL 5 METHYL 2,4(3H) PYRIMIDINEDIONE; 1 METHYL 2,4(3H) PYRIMIDINEDIONE; 1,3 DIMETHYL 2,4 PYRIMIDINEDIONE; 1,3,5 TRIMETHYL 2,4 PYRIMIDINEDIONE; 1,5 DIMETHYL 2,4(3H) PYRIMIDINEDIONE; 2 ETHOXY 3 ETHYL 2(3H) PYRIMIDINONE; 2 ETHOXY 3 ETHYL 5 METHYL 2(3H) PYRIMIDINONE; 2 ETHOXY 4 METHOXY 5 METHYLPYRIMIDINE; 2 ETHOXY 4 METHOXYPYRIMIDINE; 2,4 DIETHOXY 5 METHYLPYRIMIDINE; 2,4 DIETHOXYPYRIMIDINE; 2,4(3H) PYRIMIDINEDIONE; 3 ETHYL 2,4(1H) PYRIMIDINEDIONE; 3 ETHYL 5 METHYL 2,4(1H) PYRIMIDINEDIONE; 3 METHYL 2,4(1H) PYRIMIDINEDIONE; 3,5 DIMETHYL 2,4(IH) PYRIMIDINEDIONE; 4 ACETYLAMINO 1 ETHYL 2(1H) PYRIMIDINONE; 4 ACETYLAMINO 1 METHYL 2(1H) PYRIMIDINONE; 4 ACETYLAMINO 2 ETHOXYPYRIMIDINE; 4 ACETYLAMINO 2(1H) PYRIMIDINONE; 4 ETHOXY 1 ETHYL 2(1H) PYRIMIDINONE; 4 ETHOXY 1 ETHYL 5 METHYL 2(1H) PYRIMIDINONE; 4 METHOXY 2(1H) PYRIMIDINONE; 4 METHOXY 5 METHYL 2(1H) PYRIMIDINONE; 5 METHYL 2,4 DIMETHOXYPYRIMIDINE; PYRIMIDINE DERIVATIVE; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKYLATION; ARTICLE; METHYLATION; PRIORITY JOURNAL;

EID: 33744930889     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.04.098     Document Type: Article

References (34)

1. Amblard F., Nolan S.P., Schinazi R.F., and Agrofoglio L.A. Tetrahedron 61 (2005) 537-554
2. Bronson J.J., Ghazzouli I., Hitchcock M.J.M., Webb R.R., and Martin J.C. J. Med. Chem. 32 (1989) 1457-1463
3. Bhat S. Collect. Czech. Chem. Commun. 58 (1993) 683-690
4. Senda S., Hirota K., and Banno K. J. Med. Chem. 15 (1972) 471-476
5. Faul M.M., Huff B.E., Kaldor S.W., and Werner J.A. Tetrahedron 53 (1997) 8085-8104
6. Danel K., Larsen E., Pedersen B.E., Vestergaard B.F., and Nielsen C. J. Med. Chem. 39 (1996) 2427-2431
7. Maruenda H., and Johnson F. J. Med. Chem. 38 (1995) 2145-2151
8. Czernecki S., and Ezzitouni A. J. Org. Chem. 57 (1992) 7325-7328
9. Nawrot B., Michalak O., Olejniczak S., Wiecczorek M.W., Lis T., and Stec W.J. Tetrahedron 57 (2001) 3979-3985
10. See for example:. Hattori H., Nozawa E., Iino T., Yoshimura Y., Shuto S., Shimamoto Y., Nomura M., Fukushima M., Tanaka M., Sasaki T., and Matsuda A. J. Med. Chem. 41 (1998) 2892-2902
11. Jane D.E., Hoo K., Kamboj R., Deverill M., Bleakman D., and Mandelzys A. J. Med. Chem. 40 (1997) 3645-3650
12. Rowbottom M.W., Tucci F.C., Zhu Y.-F., Guo Z., Gross T.D., Reinhart G.J., Xie Q., Struthers R.S., Saunders J., and Chen C. Bioorg. Med. Chem. Lett. 14 (2004) 2269-2274
13. Yamauchi K., and Kinoshita M. J. Chem. Soc., Perkin Trans. 1 (1973) 391-392
14. Ogilvie K.K., and Beaucage S.L. Tetrahedron Lett. 19 (1978) 1663-1666
15. Gupta O.D., Twamley B., Kirchmeier R.L., and Shreeve J.M. J. Fluorine Chem. 106 (2000) 199-204
16. Grandjean P., Benhaddou R., Granet R., and Krausz P. Tetrahedron Lett. 38 (1997) 6185-6188
17. Wong J.L., and Fuchs D.S. J. Org. Chem. 36 (1971) 848-850
18. Kusmierek J.T., and Singer B. Nucleic Acid Res. 3 (1976) 989-1000
19. Hilbert G.E., and Johnson T.B. J. Am. Chem. Soc. 52 (1930) 2001-2007
20. Vörbruggen H., and Hofle G. Chem. Ber. 114 (1981) 1234-1286
21. Wittenburg E. Chem. Ber. 99 (1966) 2391-2398
22. Ganguly S., and Kundu K.K. Can. J. Chem. 72 (1994) 1120-1126
23. Nakanishi K., Suzuki N., and Yamazaki F. Bull. Chem. Soc. Jpn. 34 (1961) 53-57
24. Pearson R.G., and Songstad J. J. Am. Chem. Soc. 89 (1967) 1827-1836
25. Gambacorta A., Farah M.E., and Tofani D. Tetrahedron 55 (1999) 12615-12628
26. Prystas M. Collect. Czech. Chem. Commun. 40 (1975) 1786-1793
27. Function "Compute Properties", Theory PM3 in Chem3D Ultra 7.0; Cambridge Soft Corporation: Cambridge, MA, USA, 2001.
28. Ueda T., and Fox J.J. J. Org. Chem. 29 (1964) 1762-1769
29. Sakamoto T., Satoh C., Kondo Y., and Yamanaka H. Chem. Pharm. Bull. 41 (1993) 81-86
30. Reconen P., Dohta Y., KodaKa M., Okada T., Okamoto K., and Okuno H. J. Med. Chem. 40 (1997) 515-519
31. Rabinowitz J.L., and Gurin S. J. Am. Chem. Soc. 75 (1953) 5758-5759
32. Tanabe T., Yamauchi Y., and Kinoshita M. Bull. Chem. Soc. Jpn. 50 (1977) 3021-3025
33. Schmidt-Nickels W., and Johnson T.B. J. Am. Chem. Soc. 52 (1930) 4511-4516
34. Webb R.R., Wos J.A., Bronson J.J., and Martin J.C. Tetrahedron Lett. 29 (1988) 5475-5478