A General Procedure for the Synthesis of 2-Substituted Pyrimidine-5-Carboxylic Esters

Pavel Zhichkin; David J. Fairfax; Shane A. Eisenbeis

doi:10.1055/s-2002-25767

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Synthesis 2002(6): 0720-0722
DOI: 10.1055/s-2002-25767

SHORTPAPER

A General Procedure for the Synthesis of 2-Substituted Pyrimidine-5-Carboxylic Esters

Pavel Zhichkin^a, David J. Fairfax*^a, Shane A. Eisenbeis^b
^a Albany Molecular Research Inc., 21 Corporate Circle, PO Box 15098, Albany, NY 12212, USA
^b Pfizer Global Research and Development, Groton Laboratories, Pfizer Inc., Eastern Point Road, Groton, CT 06340, USA
Fax: +1(518)4640289; e-Mail: DavidF@albmolecular.com;

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Publication History

Received 6 November 2001
Publication Date:
26 April 2002 (online)

Abstract
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Abstract

A method for the synthesis of 2-substituted pyrimidine-5-carboxylic esters is described. The sodium salt of 3,3-dimethoxy-2-methoxycarbonylpropen-1-ol (3) has been found to react with a variety of amidinium salts to afford the corresponding 2-substituted pyrimidine-5-carboxylic esters.

Keywords

heterocycles - pyrimidines - condensation - amidinium salt - esters

References

1a Urban R. Schnider O. Helv. Chim. Acta 1958, 41: 1806

Google Scholar
1b Kohra S. Tominga Y. Hosomi A. J. Heterocycl. Chem. 1988, 25: 959

Google Scholar
1c Lorente A. Vaquerizo L. Martin A. Heterocycles 1995, 41: 71

Google Scholar
1d Guzman A. Romero M. Talamas FX. Villena R. Greenhouse R. Muchowski JM. J. Org. Chem. 1996, 61: 2470

Google Scholar
2a Schenore P. Sansebastiano L. Mosti L. J. Heterocycl. Chem. 1990, 27: 295

Crossref Google Scholar
2b Dyer E. Johnson TB. J. Am. Chem. Soc. 1934, 56: 222

Crossref Google Scholar
3 Gupton JT. Riesinger SW. Smith SQ. Bevirt KM. Sikorski JA. Dahl ML. Arnold A. J. Heterocycl. Chem. 1991, 28: 1281

Crossref Google Scholar
4 Ragan JA. McDermott RE. Jones BP. am Ende DJ. Clifford PJ. McHardy SJ. Heck SD. Liras S. Segelstein BE. Synlett 2000, 1172

Article in Thieme Connect Google Scholar
5 Gupton JT. Petrich S. Hicks FA. Wilkinson D. Vargus M. Hosein M. Kirsten N. Sikorski JA. Heterocycles 1998, 47: 689

Crossref Google Scholar
6a Davies IW. Taylor M. Marcoux J.-F. Wu J. Dormer PG. Hughes D. Reider PJ. J. Org. Chem. 2001, 66: 251

Crossref Google Scholar
6b Davies IW. Marcoux J.-F. Wu J. Palucki M. Corley EG. Robbins M. Tsou N. Ball RG. Dormer P. Larsen RD. Reider PJ. J. Org. Chem. 2000, 65: 4571

Crossref Google Scholar
6c Davies I. Taylor M. Hughes D. Reider PJ. Org. Lett. 2000, 2: 3385

Crossref Google Scholar
7 Sweet F. Fissekis JD. J. Am. Chem. Soc. 1973, 95: 8741

Crossref Google Scholar
8a Miller CO. Skoog F. Okumura FS. Von Saltza MH. Strong FM. J. Am. Chem. Soc. 1956, 78: 1375

Google Scholar
8b Arya VP. David J. Grewal RS. Marathe SB. Patil SD. Indian J. Chem., Sect. B 1977, 15: 1129

Google Scholar
8c Takagi K. Masaaki T. Murakami Y. Kuniyoshi O. Ishii K. Morita H. Aotsuka T. J. Heterocycl. Chem. 1987, 24: 1003

Google Scholar
8d Ple N. Turck A. Heynderickx A. Queguiner GJ. J. Heterocycl. Chem. 1997, 34: 551

Google Scholar
9 Ballard E. Johnson TB. J. Am. Chem. Soc. 1942, 64: 794

Crossref Google Scholar
10 Garcia MA. Herrera FA. Moreno JF. Munoz MPJ. Alonso MC. Subramanian LR. Tetrahedron 1996, 52: 7973

Crossref Google Scholar
11 Angiolelli ME. Casalnuovo AL. Selby TE. Synlett 2000, 905

Article in Thieme Connect Google Scholar
12 May CD. Sykes P. J. Chem. Soc. C 1966, 649

Crossref Google Scholar
13 Guzman A. Romero M. Talamas FX. J. Org. Chem. 1996, 61: 2470

Google Scholar
14 Budesinky Z. Vavrina J. Collect. Czech. Chem. Commun. 1972, 37: 1720

Google Scholar
15 Schwan T. J. Heterocycl. Chem. 1977, 14: 695

Google Scholar