Syntheses of 2-amino-4,6-dichloro-5-nitropyrimidine and 2-amino-4,5,6-trichloropyrimidine: an unusual aromatic substitution

Tetrahedron Letters

Volumn 50, Issue 44, 2009, Pages 6022-6024

  Lopez, Sergio ^a   McCabe, Thomas ^a   Stanley McElhinney, R ^a   McMurry, T Brian H ^a   Rozas, Isabel ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4,5,6 TRICHLOROPYRIMIDINE; 2 AMINO 4,6 DICHLORO 5 NITROPYRIMIDINE; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DNA REPAIR; NITRATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 70149101577     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.08.029     Document Type: Article

References (20)

1. McElhinney R.S., McMurry T.B.H., and Margison G.P. Mini Rev. Med. Chem. 3 (2003) 123
2. McElhinney R.S., Donnelly D.J., McCormick J.E., Kelly J., Watson A.J., Rafferty J.A., Elder R.H., Middleton M.R., and Willington M.A. J. Med. Chem. 41 (1998) 5265
3. Ranson M., Middleton M.R., Bridgewater J., Lee S.M., Dawson M., Jowle D., Halbert G., Waller S., McGrath H., Gumbril L., McElhinney R.S., McMurry T.B.H., and Margison G.P. Clin. Cancer Res. 12 (2006) 1577
4. McMurry T.B.H. DNA Repair 6 (2007) 1161
5. Norbeck, D. W.; Rosen, T. J.; Sham, H. L. US Patent, 1991, US4988703; Chem. Abstr. 1991, 115, 50218.
6. Temple Jr. C., Smith B.H., and Montgomery J.A. J. Org. Chem. 40 (1975) 3141
7. Chae M., Swenn K., Kanugula S., Dolan M.E., Pegg A.E., and Moschel R.C. J. Med. Chem. 38 (1995) 359
8. Terashima I., and Kohda K. J. Med. Chem. 41 (1998) 503
9. Pfleiderer W., and Lohrmann R. Chem. Ber. 94 (1961) 2708
10. Boyle P.H., Daly K.M., Leurquin F., Robinson J.K., and Scully D.T. Tetrahedron Lett. 42 (2001) 1793
11. Hazebroucq G. Ann. Pharm. 24 (1966) 793
12. Bell L., McGuire H.M., and Freeman G.A. J. Heterocycl. Chem. 20 (1983) 41
13. Hepburn D.R., and Hudson H.R. Chem. Ind. (1974) 664
14. Seela F., and Steker H. Helv. Chim. Acta 69 (1986) 1602
15. Bunnett J.F., and Zahler R.E. Chem. Rev. 49 (1951) 273
16. Denisov A.Y., Krivopalov V.P., Mamatyuk V.I., and Mamaev V.P. Magn. Reson. Chem. 26 (1988) 42
17. Riand J., Chenon M.T., and Lumbroso-Bader N. Tetrahedron Lett. (1974) 2123
18. Temple Jr. C., McKee R.L., and Montgomery J.A. J. Org. Chem. 27 (1962) 1671
19. Temple Jr. C., McKee R.L., and Montgomery J.A. J. Org. Chem. 30 (1965) 829
20. Temple Jr. C., Coburn Jr. W.C., Thorpe M.C., and Montgomery J.A. J. Org. Chem. 30 (1965) 2395 and references cited therein