Facile synthesis of 7-amino anilinoquinazolines via direct amination of the quinazoline core

Tetrahedron Letters

Volumn 46, Issue 43, 2005, Pages 7381-7384

  Harris, Craig S ^a   Kettle, Jason G ^a   Williams, Emma J ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Direct amination; Triflate

Indexed keywords

FLUORINE DERIVATIVE; QUINAZOLINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

AMINATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRECURSOR;

EID: 25444469410     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.123     Document Type: Article

References (18)

1. J.R. Woodburn Pharmacol. Ther. 82 1999 241
2. J.R. Woodburn, A.J. Barker, K.H. Gibson, S.E. Ashton, and A.E. Wakeling Proc. Am. Assoc. Cancer Res. 38 1997 6333
3. A.D. Laird, and J.M. Cherrington Expert Opin. Invest. Drugs 12 2003 51
4. For recent articles see: H.J. Broxterman, and N.H. Georgopapadakou Drug Resist. Updates 7 2004 79 87
5. J.G. Paez, P.A. Jänne, J.C. Lee, S. Tracy, H. Greulich, S. Gabriel, P. Herman, F.J. Kaye, N. Lindeman, T.J. Boggon, K. Naoki, H. Sasaki, Y. Fujii, M.J. Eck, W.R. Sellers, B.E. Johnson, and M. Meyerson Science 304 2004 1497
6. T.J. Lynch, D.W. Bell, R. Sordella, S. Gurubhagavatula, R.A. Okimoto, B.W. Brannigan, P.L. Harris, S.M. Haserlat, J.G. Supko, F.G. Haluska, D.N. Louis, D.C. Christiani, J. Settleman, and D.A. Haber New Eng. J. Med. 350 2004 2129
7. Starting from commercially-available vanillic acid, a similar process was used to access 3 as described by A. Pandey, D. Volkots, J.M. Sergooy, J.W. Rose, J.-C. Yu, J.L. Lambing, A. Hutchaleelaha, S.J. Hollenbach, K. Abe, N.A. Giese, and R.M. Scarborough J. Med. Chem. 45 2002 3772
8. J.B. Hendrickson, and R. Bergeron Tetrahedron Lett. 14 1973 4607
9. 3 (Aldrich -325 mesh, 3.00 equiv) in THF (5 ml/g), was added solid phenyl-N(bis) trifluoromethanesulfonamide (1.01 equiv). The slurry was stirred at ambient temperature for 4 h. The slurry was filtered through a bed of Celite and concentrated on a rotary evaporator to afford a thick viscous oil which was recrystallised from ice-cold methanol (3 ml/g) to afford the triflate (88%) as an off-white solid.
10. Gilday, J. P.; Moody, D. PCT Int. Appl. WO 2004024703, 2004.
11. For review articles see: J.P. Wolfe, S. Wagaw, J.-F. Marcoux, and S.L. Buchwald Acc. Chem. Res. 31 1998 805 818
12. J.F. Hartwig Ang. Chem. Int., Ed. 32 1998 2046
13. For a high-pressure preparative procedure see H. Kotsuki, S. Kobayashi, H. Suegna, and N. Nishiwaza Synthesis 1990 1145
14. S. Ding, N.S. Gray, X. Wu, O. Ding, and P.G. Schultz J. Am. Chem. Soc. 124 2002 1594
15. M. Tobe, Y. Isobe, H. Tomizawa, M. Matsumoto, F. Obara, T. Nagasaki, and H. Hayashi Bioorg. Med. Chem. Lett. 11 2001 545
16. 3-MeOH-DCM gradient.
17. When the triflate is added at 135°C, attack at sulfur in the first part of the equilibrium is to a degree by-passed and the desired products can be isolated, in certain cases, in yields as high as 20%.
18. 3-MeOH-DCM gradient.