Development of new amination reaction at 4-position of pyrimidine nucleosides.
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).
Tsuchiya
Katsutoshi
K
Organic Synthesis Group, Catalysis Science Laboratory, Mitsui Chemicals, INC., 580-32 Nagaura, Sodegaura-City, Chiba 299-0265, Japan.
Komatsu
Hironori
H
D000586:Amination; D011741:Pyrimidine Nucleosides / Q000737:chemistry*
D011741:Pyrimidine Nucleosides