Heterocyclic polyfluoro-compounds. Part XVI. 2,4,5-Trifluoro-6-iodopyrimidine

Abstract

Reaction of tetrafluoropyrimidine with sodium iodide in dimethylformamide yields 2,4,5-trifluoro-6-iodopyrimidine 2,5-difluoro-4,6-di-iodopyrimidine, and traces of 2,4,5-trifluoropyrimidine, when terafluoropyrimidine is gether with 2,5-difluoropyrimidine and small amount of 4,5,6-trifluoropyrimidine, when tetrafluoropyrimidine is treated with lithium aluminium hydride. Methoxide ion and ammonia attack 2,4,5-trifluoro-6-iodopyrimidine at the 4-position to yield the corresponding substituted 2,5-difluoroiodopyrimidines; coupling of the 6-iodo-compound by the Ullmann technique affords perfluoro-4,4′-bipyrimidyl, Attempts to convert 2,4,5-trifluoro-6-iodopyrimidine into the corresponding Grignard reagent failed.