An expeditious synthesis of 6-Amido-(1H,3H)-Pyrimidine- 2,4-Diones from Uracil-6-Carboxylic Acid

Md Wahab Khan; Md Enamul Haque; Md Faiaz Ahmed

doi:10.3329/dujps.v13i1.21856

An expeditious synthesis of 6-Amido-(1H,3H)-Pyrimidine- 2,4-Diones from Uracil-6-Carboxylic Acid

Authors

Md Wahab Khan Department of Chemistry, Bangladesh University of Engineering & Technology (BUET), Dhaka-1000
Md Enamul Haque Department of Chemistry, Bangladesh University of Engineering & Technology (BUET), Dhaka-1000
Md Faiaz Ahmed Department of Chemistry, Bangladesh University of Engineering & Technology (BUET), Dhaka-1000

DOI:

https://doi.org/10.3329/dujps.v13i1.21856

Keywords:

Pyrimidine, uracil, orotic acid, phosphorus oxychloride, arylamines, antiviral

Abstract

2,4-Dichloro pyrimidine-6-carbonylchloride (2) was synthesized by refluxing uracil-6-carboxylic acid (orotic acid) with phosphorus oxychloride and phosphorus pentachloride. Compound (2) underwent a smooth coupling reaction with a number of substituted arylamines to yield 2, 4-dichloro-6-amidopyrimidines (8-12) which were converted to the corresponding 2, 4-dimethoxy-6-amidopyrimidines (13-17) on treatment with sodium methoxide in methanol. Compounds 13-17 afforded 6-amido-(1H, 3H)-pyrimidine-2, 4-diones (18-22) in good yield on refluxing with 6 M hydrochloric acid. These pyrimidinone derivatives may exhibit antiviral actitities.

DOI: http://dx.doi.org/10.3329/dujps.v13i1.21856

Dhaka Univ. J. Pharm. Sci. 13(1): 23-29, 2014 (June)

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Published

2015-02-03

How to Cite

Khan, M. W., Haque, M. E., & Ahmed, M. F. (2015). An expeditious synthesis of 6-Amido-(1H,3H)-Pyrimidine- 2,4-Diones from Uracil-6-Carboxylic Acid. Dhaka University Journal of Pharmaceutical Sciences, 13(1), 23–29. https://doi.org/10.3329/dujps.v13i1.21856