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Facilitation of addition–elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol
Hayley J. Whitfield,Roger J. Griffin,Ian R. Hardcastle,Andrew Henderson,Jerome Meneyrol,Veronique Mesguiche,Kerry L. Sayle,Bernard T. Golding
Chemical Communications Pub Date : 10/14/2003 00:00:00 , DOI:10.1039/B308948G
Abstract

SNAr displacement reactions of 6-cyclohexylmethoxy-2-fluoropurine, 6-amino-2-butylsulfonyl-4-cyclohexylmethoxypyrimidine and 2-amino-6-chloropurine with substituted anilines (e.g. the weakly nucleophilic 4-aminobenzenesulfonamide) are dramatically accelerated in the presence of trifluoroacetic acid and occur especially efficiently in 2,2,2-trifluoroethanol solvent.

Graphical abstract: Facilitation of addition–elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol
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