Synthesis of pyrimidines by direct condensation of amides and nitriles

Nature Protocols

Volumn 2, Issue 8, 2007, Pages 2018-2023

  Movassaghi, Mohammad ^a   Hill, Matthew D ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; AMIDE; HETEROCYCLIC COMPOUND; NITRILE; PYRIMIDINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; METHODOLOGY; POLYMERIZATION; PRIORITY JOURNAL; PYRIMIDINE SYNTHESIS;

AMIDES; CHEMISTRY, ORGANIC; NITRILES; PYRIMIDINES;

EID: 34548146136     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2007.280     Document Type: Article

References (22)

1. Undheim, K. & Benneche, T. Pyrimicines and their benzo derivatives. In Comprehensive Heterocyclic Chemistry II Vol. 6 (eds. Katritzky, A.R., Rees, C.W., Scriven, E.F.V. & McKillop, A.) 93-231, 1177-1307 (Pergamon, Oxford, 1996).
2. Lagoja, I.M. Pyrimidine as constituent of natural biologically active compounds. Chem. Biodivers. 2, 1-50 (2005).
3. Michael, J.P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 22, 627-646 (2005).
4. Erian, A.W. The chemistry of β-enaminonitriles as versatile reagents in heterocyclic synthesis. Chem. Rev. 93, 1991-2005 (1993).
5. Sakai, N., Youichi, A., Sasada, T. & Konakahara, T. New approach to the practical synthesis of tri- or tetrasubstituted pyrimidine derivatives: a four-component coupling reaction from a functionalized silane, two types of aromatic nitriles, and acetals. Org. Lett. 7, 4705-4708 (2005).
6. Yoon, D.S. et al. Efficient synthesis of 4-aminoquinazoline and thieno[3,2-d] pyrimidin-4-ylamine derivatives by microwave irradiation. Org. Lett. 6, 4775-4778 (2004).
7. Kakiya, H., Yagi, K., Shinokubo, H. & Oshima, K. Reaction of α,α-dibromo oxime ethers with Grignard reagents: Alkylative annulation providing a pyrimidine core. J. Am. Chem. Soc. 124, 9032-9033 (2002).
8. Kotsuki, H., Sakai, H., Morimoto, H. & Suenaga, H. A new quinazoline synthesis. Synlett 1993-1995 (1999).
9. Ghosez, L., Jnoff, E., Bayard, P., Sainte, F. & Beaudegnies, R. A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2 + 2 + 2] strategy. Tetrahedron 55, 3387-3400 (1999).
10. Martínez, A.G., Fernández, A.H., Fraile, A.G., Subramanian, L.R. & Hanack, M. On the mechanism of the reaction between ketones and trifluoromethanesulfonic anhydride. An improved and convenient method for the preparation of pyrimidines and condensed pyrimidines. J. Org. Chem. 57, 1627-1630 (1992).
11. Chinchilla, R., Nájera, C. & Yus, M. Metalated heterocycles and their applications in synthetic organic chemistry. Chem. Rev. 104, 2667-2722 (2004).
12. Turck, A., Plé, N., Mongin, F. & Quéguiner, G. Advances in the directed metalation of azines and diazines (pyridines, pyrimidines, pyrazines, pyridazines, quinolines, benzodiazines and carbolines). Part 2. Metalation of pyrimidines, pyrazines, pyridazines and benzodiazines. Tetrahedron 57, 4489-4505 (2001).
13. Movassaghi, M. & Hill, M.D. Single-step synthesis of pyrimidine derivatives. J. Am. Chem. Soc. 128, 14254-14255 (2006).
14. Muci, A.R. & Buchwald, S.L. Practical palladium catalysts for C-N and C-0 bond formation. Top. Curr. Chem. 219, 131-209 (2002).
15. Hartwig, J.F. Palladium-catalyzed amination of aryl halides and related reactions. In Handbook of Organopalladium Chemistry for Organic Synthesis (ed. Negishi, E.) 1051-1096 (Wiley-Interscience, New York, 2002).
16. Dehli, J.R., Legros, J. & Bolm, C. Synthesis of enamines, enol ethers, and related compounds by crosscoupling reactions. Chem. Commun. 8, 973-986 (2005).
17. Beletskaya, I.P. & Cheprakov, A.V. Copper in cross-coupling reactions. Coordin. Chem. Rev. 248, 2337-2364 (2004).
18. Jiang, L., Job, G.E., Klapars, A. & Buchwald, S.L. Copper-catalyzed coupling of amides and carbamates with vinyl halides. Org. Lett. 5, 3667-3669 (2003).
19. Bose, D.S. & Jayalakshmi, B. A practical method for the preparation of nitriles from primary amides under non-acidic conditions. Synthesis 64-65 (1999).
20. Movassaghi, M. & Hill, M.D. Synthesis of substituted pyridine derivatives via the ruthenium-catalyzed cycloisomerization of 3-azadienynes. J. Am. Chem. Soc. 128, 4592-4593 (2006).
21. Hill, M.D. & Movassaghi, M. Synthesis of substituted pyridines and quinolines. Synthesis 1115-1119 (2007).
22. Charette, A.B. & Grenon, M. Spectroscopic studies of the electrophilic activation of amides with triflicanhydride and pyridine. Can. J. Chem. 79, 1694-1703 (2001).