Study on the synthesis of 6-alkylaminouridines via the nucleophilic aromatic substitution reaction of 6-cyanouridine derivatives

• Published in: Tetrahedron letters Vol. 52; no. 31; pp. 3969 - 3972
• Main Authors: Lin, Jian-Bang, He, Jhih-Li, Shih, Yu-Chiao, Chien, Tun-Cheng
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 03.08.2011; Elsevier
• Subjects: 6-Alkylaminouracil; 6-Alkylaminouridine; 6-Cyanouracil; 6-Cyanouridine; Amines; Catalysis; Catalysts; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Derivatives; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Nucleophilic aromatic substitution; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Substitution reactions; Synthesis (chemistry); Tetrahedrons; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; 6-Alkylaminouracil; Nucleophilic aromatic substitution; 6-Cyanouracil; 6-Alkylaminouridine; 6-Cyanouridine; PYRIMIDINE-DERIVATIVES; 6-CYANO-1,3-DIMETHYLURACIL; CONVERSION; NUCLEOSIDES; URIDINE; ANTITUMOR; OROTIDINE MONOPHOSPHATE DECARBOXYLASE; 3-ISOXANTHOSINE; OROTIDINE-5'-MONOPHOSPHATE DECARBOXYLASE; INHIBITORS; Nitrile; Nitrogen heterocycle; Selectivity; Uracile derivatives; Chemical substitution; Pyridine derivatives; Pyrimidine base; Uridine; Pyrimidine derivatives; Nucleoside; Ribonucleoside; Nucleophilic substitution; Chemical synthesis; Primary amine; Catalyst; SNAr mechanism
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.05.033

6-Cyanouracil derivatives underwent direct substitution reactions with selective primary amines in the presence of N, N-dimethylaminopyridine as a catalyst to give the corresponding 6-alkylaminouracils. This reaction provides a facile access to versatile 6-alkylaminouridine derivatives.