Development of new amination reaction at 4-position of pyrimidine nucleosides | Zendy

Kazuhiko Tsuchiya | Zendy; H. Komatsu | Zendy

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Development of new amination reaction at 4-position of pyrimidine nucleosides

Author(s) -

Kazuhiko Tsuchiya,

H. Komatsu

Publication year - 2002

Publication title -

nucleic acids symposium series

Language(s) - English

Resource type - Journals

eISSN - 1746-8272

pISSN - 0261-3166

DOI - 10.1093/nass/2.1.135

Subject(s) - pyrimidine , amination , chemistry , reductive amination , ammonium chloride , nucleoside , ammonium , organic chemistry , medicinal chemistry , stereochemistry , catalysis

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).

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