Bromination at C-5 of pyrimidine and C-8 of purine nucleosides with 1, 3-dibromo-5, 5-dimethylhydantoin

R Rayala, SF Wnuk

Index: Rayala, Ramanjaneyulu; Wnuk, Stanislaw F. Tetrahedron Letters, 2012 , vol. 53, # 26 p. 3333 - 3336

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Citation Number: 20

Abstract

Treatment of the protected and unprotected nucleosides with 1, 3-dibromo-5, 5- dimethylhydantoin in aprotic solvents such as CH2Cl2, CH3CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced the efficiency of bromination.