A facile synthesis of 5-(perfluoroalkyl)-pyrimidines

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 perfluoroalkyliodides in polar aprotic solvents, such as DMSO, and under inert conditions....

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Bibliographic Details
Published in:Nucleic acids research 1975-11, Vol.2 (11), p.2183-2192
Main Authors: Cech, D., Wohlfeil, R., Etzold, G.
Format: Article
Language:English
Subjects:
Deoxyuridine - analogs & derivatives
Fluorine
Methods
Pyrimidinones - chemical synthesis
Uracil - analogs & derivatives
Uridine - analogs & derivatives
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Summary: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 perfluoroalkyliodides 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 perfluoroalkyl 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.
ISSN:0305-1048
1362-4962
DOI:10.1093/nar/2.11.2183