A facile synthesis of 5-Iodo-6-substituted Pyrimidines from Uracil-6-Carboxylic acid (Orotic acid)

Authors

  • Tanvir Sultana Department of Chemistry, Bangladesh University of Engineering and Technology, Dhaka-1000
  • Md Wahab Khan Department of Chemistry, Bangladesh University of Engineering and Technology, Dhaka-1000

DOI:

https://doi.org/10.3329/dujps.v12i2.17613

Keywords:

Synthesis, 5-Iodo-6-Substituted pyrimidines, Orotic acid

Abstract

2,4-Dichloro-pyrimidine-6-carbonylchloride (2) was synthesized by refluxing orotic acid (1) with phosphorus oxychloride and phosphorus pentachloride. Compound (2) underwent a smooth Friedel-Craft's reaction with a number of substituted benzene to yield 2,4-Dichloro-6-aroylpyrimidines 6 and 7 which were converted to the corresponding dimethoxy pyrimidines (8, 9) on treatment with sodium methoxide in methanol. The iodination reaction on 2,4-dimethoxy-6-aroylpyrimidines (8, 9) was attempted by several methods but only NIS-TFA-TFAA method gave the desired products, 2,4-dimethoxy-5-iodo-6-aroylpyrimidine (10, 11) in good yields.

Dhaka Univ. J. Pharm. Sci. 12(2): 97-102, 2013 (December)

DOI: http://dx.doi.org/10.3329/dujps.v12i2.17613

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Published

2014-01-12

How to Cite

Sultana, T., & Khan, M. W. (2014). A facile synthesis of 5-Iodo-6-substituted Pyrimidines from Uracil-6-Carboxylic acid (Orotic acid). Dhaka University Journal of Pharmaceutical Sciences, 12(2), 97–102. https://doi.org/10.3329/dujps.v12i2.17613

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