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Development of new amination reaction at 4-position of pyrimidine nucleosides
Katsutoshi Tsuchiya1, Hironori Komatsu
1Organic Synthesis Group, Catalysis Science Laboratory, Mitsui Chemicals, INC., 580-32 Nagaura, Sodegaura-City, Chiba 299-0265, Japan.
Nucleic Acids Research. Supplement (2001)
|August 9, 2003
Abstract:
A new method for the syntheses of the 4-amino-pyrimidine nucleosides (1a, b) has been developed. The method consists of conversion of uridines into quaternary-ammonium intermediates (4a, b) by the reaction with p-toluenesulfonyl chloride(TsCl) in the presence of tertiary-amines, followed by amination with aq NH3. The method is expedient for large-scale preparation of cytidines like 2'-deoxycytidine (1a) or 2'-deoxy-5-methylcytidine (1b).