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 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.
D003857:Deoxyuridine / Q000031:analogs & derivatives*; D005461:Fluorine; D008722:Methods; D011744:Pyrimidinones / Q000138:chemical synthesis*; D014498:Uracil / Q000031:analogs & derivatives*; D014529:Uridine / Q000031:analogs & derivatives*
D011744:Pyrimidinones; D005461:Fluorine; D014498:Uracil; D003857:Deoxyuridine; D014529:Uridine