155-11-3Relevant articles and documents
Synthesis of 5-Fluorocytosine Using 2-Cyano-2-fluoroethenolate as a Key Intermediate
Dietz, Jule-Philipp,Derstine, Brenden P.,Ferenc, Dorota,Crawford, Evan T.,Arduengo, Anthony J.,Gupton, B. Frank,McQuade, D. Tyler,Opatz, Till
, p. 5519 - 5526 (2019)
There is an urgent demand for 5-fluorocytosine (5-FC) due to its activity against HIV-induced fungal infections as well as its use as a key intermediate in the synthesis of the clinically highly important anti-HIV drug emtricitabine (FTC). We report a simple, low-cost five steps synthesis of 5-FC starting from chloroacetamide. Overall yields up to 46 % were achieved and the route is devoid of any chromatographic purifications. The previously unknown key intermediate (Z)-2-cyano-2-fluoroethenolate is obtained through a Claisen-type condensation from fluoroacetonitrile. As the direct cyclization with urea only gave poor yields, 5-fluoro-2-methoxypyrimidin-4-amine, 5-fluoro-2-(methylsulfanyl)pyrimidin-4-amine and 5-fluoropyrimidine-2,4-diamine served as synthetic intermediates.
2-CYANO-2-FLUOROETHENOLATE SALTS (CFES): VERSITILE ACTIVE PHARMACEUTICAL INTERMEDIATES
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Paragraph 0010, (2020/08/30)
The present invention relates to new enolate structures with utility as active pharmaceutical intermediates for the preparation of efficacious drugs such as those derived from 5-fluorocytosine (5-FC).