Skip to main content
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1975 Nov;2(11):2183–2192. doi: 10.1093/nar/2.11.2183

A facile synthesis of 5-(perfluoroalkyl)-pyrimidines.

D Cech, R Wohlfeil, G Etzold
PMCID: PMC343583  PMID: 1052538

Abstract

In the paper a synthetic two stage procedure is described for the preparation of perfluoroalkylated derivatives of uracil and its nucleosides. Using copper bronze a perfluoroalkyl-copper-complex is formed from perfluoralkyl iodides in polar aprotic solvents, such as DMSO, and under inert conditions. The reaction of this complex with uracil, uridine and 2-deoxyuridine leads to the corresponding 5-substituted perfluoralkyl derivatives. It is shown by mass spectra that the substitution always takes place at the 5-position of the pyrimidine. The chemical and physical properties of the formed compounds are described.

Full text

PDF
2183

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. MERTES M. P., SAHEB S. E. Use of sulfur tetrafluoride in syntheses of potential anticancer agents. J Pharm Sci. 1963 May;52:508–509. doi: 10.1002/jps.2600520531. [DOI] [PubMed] [Google Scholar]
  2. Nestler H. J., Garrett E. R. Prediction of stability in pharmaceutical preparations. XV. Kinetics of hydrolysis of 5-trifluoromethyl-2'-deoxyuridine. J Pharm Sci. 1968 Jul;57(7):1117–1125. doi: 10.1002/jps.2600570706. [DOI] [PubMed] [Google Scholar]
  3. REYES P., HEIDELBERGER C. FLUORINATED PYRIMIDINES. XXV. THE INHIBITION OF THYMIDYLATE SYNTHETASE FROM EHRLICH ASCITES CARCINOMA CELLS BY PYRIMIDINE ANALOGS. Biochim Biophys Acta. 1965 May 11;103:177–179. [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES