474901-41-2Relevant academic research and scientific papers
Treatment of polyfluoro-1,1-dihydroalkyl sulfones with sodium cyanate and triethylamine: A new method for the synthesis of 6-(polyfluoroalkyl)uracils
Timoshenko, Vadim M.,Nikolin, Yarema V.,Chernega, Alexander N.,Shermolovich, Yuriy G.
, p. 1619 - 1627 (2002)
Polyfluoro-1,1-dihydroalkyl benzyl sulfones 1 reacted with sodium cyanate in the presence of Et3N to give triethylammonium salts of uracil derivatives 2. The structure of 2b was established by X-ray determination. Acidification of compounds 2 with aqueous HCl gave 5-(benzylsulfonyl)-6-(polyfluoroalkyl)pyrimidine-2,4(1H,3H)-diones 3. Alkylation of compounds 3 with CH3I afforded products methylated at N-2, confirmed by X-ray diffraction. Treatment of 3 with PCl5 gave dichloropyrimidines 7. The chlorine atoms in compounds 7 with polyfluoroalkyl substituents of different lengths showed differing reactivities in reactions with ammonia and methanol. The sites of substitution of chlorine atoms in 7 were elucidated by X-ray studies. Direct amination of 3 occurred together with desulfonylation on heating in HMPA, with formation of 6-(polyfluoroalkyl)-substituted 2,4-bis(dimethylamino)pyrimidines 13. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
