A novel route to 2,4-dianilino-substituted pyrimidines

Tetrahedron Letters

Volumn 51, Issue 3, 2010, Pages 543-544

  Leenders, Ruben ^a   Heeres, Jan ^b   Guillemont, Jérôme ^c   Lewi, Paul ^b  

^a Mercachem BV   (Netherlands)

^b JANSSEN RESEARCH FOUNDATION   (Belgium)

^c JOHNSON AND JOHNSON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; PYRIMIDINE 2,4 BIS(TRIFLUOROMETHANESULFONATE); PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON TRANSPORT; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 71649088294     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.094     Document Type: Article

References (13)

1. Some of the compounds described in this Letter were claimed in Kukla, M. J.; Ludovici, D. W.; Kavash, R. W.; De Corte, B. L. D.; Heeres, J.; Janssen, P. A. J.; Koymans, L. M. H.; De Jonge, M. R.; Van Aken, K. J. A.; Krief, A.; Leenders, R. G. G. U.S. 7276510, 2007; Chem. Abstr. 2001, 135, 371765. The synthesis of the compounds from route C (Scheme 3) were not described in this patent.
2. Ludovici D.W., De Corte B.L., Kukla M.J., Ye H., Ho C.Y., Lichtenstein M.A., Kavash R.W., Andries K., de Béthune M.-P., Azijn H., Pauwels R., Lewi P.J., Heeres J., Koymans L.M.H., De Jonge M.R., Van Aken K.J.A., Daeyaert F.F.D., Das K., Arnold E., and Janssen P.A.J. Bioorg. Med. Chem. Lett. 11 (2001) 2235
3. De Corte, B.; De Jonge, M. R.; Heeres, J.; Ho, C. Y.; Janssen, P. A. J.; Kavash, R. W.; Koymans, L. M. H.; Kukla, M. J.; Ludovici, D. W.; Van Aken, K. J. A. WO 2000/27825; Chem. Abstr. 2000, 132, 347578.
4. Kukla, M. J.; Ludovici, D. W.; Kavash, R. W.; De Corte, B. L. D.; Heeres, J.; Janssen, P. A. J.; Koymans, L. M. H.; De Jonge, M. R.; Van Aken, K. J. A.; Krief, A. U.S. 7034019; Chem. Abstr. 2001, 135, 371756.
5. Schils, D. P. R.; Willems, J. J. M.; Medaer, B. P. A. M.; Pasquier, E. T. J.; Janssen, P. A. J.; Heeres, J.; Leenders, R. G. G. WO 2004/016581; Chem. Abstr. 2004, 140, 199342.
6. Guillemont, J. E. G.; Paugam, M.; Delest, B. F. M. Patent WO 2007/113254; Chem. Abstr. 2007, 147, 427364.
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10. 3, toluene, 80 °C]. However, no trace of the desired product was found using any of these conditions.
11. 3): δ = 6.38 (s, 1H), 7.70 (br s, 4H). The product was used as such.
12. 2O and EtOAc. The organic extract was dried, evaporated and the residue was purified by column chromatography (EtOAc-heptane) to give the product methyl esters D in 60-80% yield.
13. Breuninger, D.; Bastiaans, H. M. M.; Von Deyn, W.; Langewald, J. WO 2008/125410; Chem. Abstr. 2008, 149, 464751.