Facilitation of addition-elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol

Chem Commun (Camb). 2003 Nov 21:(22):2802-3. 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 dramaticallyaccelerated in the presence of trifluoroacetic acid and occur especially efficiently in 2,2,2-trifluoroethanol solvent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Purines / chemistry*
  • Pyrimidines / chemistry*
  • Solvents / chemistry
  • Trifluoroacetic Acid / chemistry*
  • Trifluoroethanol / chemistry*

Substances

  • Purines
  • Pyrimidines
  • Solvents
  • Trifluoroethanol
  • Trifluoroacetic Acid