Synthesis and regioselective transformations of ethoxy-substituted 5-(perfluoroalkyl)pyrimidines

Abstract

The reaction of 5-bromo-2,4-diethoxypyrimidine or 5-bromo-2- ethoxypyrimidine with a perfluoroalkyl iodide in the presence of Cu-bronze followed by acid hydrolysis of the resultant 5-perfluoroalkyl derivative furnishes the respective 5-perfluoroalkyluracil and 5-perfluoroalkylpyrimidin- 2(1H)one. The treatment of the perfluoroalkyluracil with NaOH or sodium alkoxide gives the respective 5-(perfluoroacyl)- or 5-(1,1-dialkoxyperfluoroalkyl)- substituted uracil. 5-(Perfluoroalkyl)pyrimidine-2(1H)one is inert under these conditions.