Single-step synthesis of pyrimidine derivatives

Journal of the American Chemical Society

Volumn 128, Issue 44, 2006, Pages 14254-14255

  Movassaghi, Mohammad ^a   Hill, Matthew D ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLOROPYRIDINE; AMIDE; BENZAMIDE; CYCLOHEXANE DERIVATIVE; CYCLOHEXANECARBONITRILE; LEWIS ACID; NITRILE; PYRIMIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; SYNTHESIS;

AMIDES; CHEMISTRY, PHARMACEUTICAL; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; NITRILES; PYRIMIDINES; STEREOISOMERISM;

EID: 33750691360     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066405m     Document Type: Article

References (35)

1. For reviews, see (a) Undheim, K.; Benneche, T. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., McKillop, A., Eds.; Pergamon: Oxford, 1996; Vol. 6, p 93.
2. (b) Lagoja, I. M. Chem. Biodiversity 2005, 2, 1.
3. (c) Michael, J. P. Nat. Prod. Rep. 2005, 22, 627.
4. (d) Joule, J. A.; Mills, K. In Heterocyclic Chemistry, 4th ed.; Blackwell Science Ltd.: Cambridge, MA, 2000; p 194.
5. (e) Erian, A. W. Chem. Rev. 1993, 93, 1991.
6. For representative reports, see (a) Sakai, N.; Youichi, A.; Sasada, T.; Konakahara, T. Org. Lett. 2005, 7, 4705.
7. (b) Yoon, D. S.; Han, Y.; Stark, T. M.; Haber, J. C.; Gregg, B. T.; Stankovich, S. B. Org. Lett. 2004, 6, 4775.
8. (c) Kakiya, H.; Yagi, K.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2002, 124, 9032.
9. (d) Kotsuki, H.; Sakai, H.; Morimoto, H.; Suenaga H. Synlett 1999, 1993.
10. (e) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387.
11. (f) Martínez, A. G.; Fernández, A. H.; Fraile, A. G.; Subramanian, L. R.; Hanack, M. J. Org. Chem. 1992, 57, 1627.
12. For reviews, see (a) Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
13. (b) Turck, A.; Plé, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489.
14. (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
15. (b) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051.
16. (c) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
17. (d) Dehli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973.
18. Movassaghi, M.; Hill, M. D. J. Am. Chem. Soc. 2006, 128, 4592.
19. 2O and pyridine, see (a) Charette, A. B.; Grenon, M. Can. J. Chem. 2001, 79, 1694.
20. (b) Charette, A. B.; Mathieu, S.; Martel, J. Org. Lett. 2005, 7, 5401.
21. (a) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
22. (b) Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc. 2000, 122, 4269.
23. Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077.
24. 4) of imidoyl chloride derivatives, see (a) Zielinski, W.; Kudelko, A. Monatsh. Chem. 2000, 131, 895.
25. (b) Kofanov, E. R.; Sosnina, V. V.; Danilova, A. S.; Korolev, P. V. Zh. Prik. Khim. 1999, 72, 813.
26. (c) Madrofiero, R.; Vega, S. Synthesis 1987, 628.
27. (a) The yield of entries 3 and 6 in Table 2 using condition B was 30 and 31%, respectively.
28. (b) Absence of nitrile during activation of the amide substrate in entry 18 of Table 2 afforded the product in 62% yield.
29. (c) The yield of entries 9, 17, 20, and 21 in Table 2 using 1.1 equiv of nitrile was 56, 70, 56, and 37%, respectively.
30. See Supporting Information for details.
31. The use of the N-4-methoxyphenyl variant of the amide in entry 21 of Table 2 provided the corresponding quinazoline in 58% yield but with complete racemization. Please see Supporting Information for details.
32. Bose, D. S.; Jayalakshmi, B. Synthesis 1999, 64.
33. 2O and 2-ClPyr under the reaction conditions was confirmed independently.
34. Ritter, J. J.; Minieri, P. P. J. Am. Chem. Soc. 1948, 70, 4045.
35. The conversion of 6 to 3 may be facilitated by net addition of 2-chloropyridinium triflate to the nitrilium ion.