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Nucleic Acids Research, 1975, Vol. 2, No. 11 2183-2192
© 1975

Articles

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

D. Cech, R. Wohlfeil and G. Etzold++

Humboldt-University Berlin, Department of Chemistry 104 Berlin, GDR

Received October 15, 1975.

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.

+ A part of this paper was presented at the 3 rd Symposium on the Chemistry of Nucleic Acid Components, October 8–12, 1975, Liblice Castle, Czechoslovakia

++ Academy of Sciences of G.D.R., Central Institute of Molecular Biology, 1115 Berlin-Buch, G.D.R.


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