This study focuses on the attempt to directly substitute the hydroxyl group of 3'-Azido-3'-deoxythymidine (AZT) with a cyano group via a �one pot� procedure, effectively eliminating the inconvenient and problematic need for isolating a substituted intermediate before introducing a nitrile source.  AZT, which is the primary starting material in an overall synthetic process of developing an oligonucleotide analogue for possible application in antisense technology, was first treated with a combination of sodium cyanide as well as TsIm, tetrabutylammonium iodide, and triethylamine as suggested in contemporary literature, but results proved unfavorable and different reagent mixtures were explored using thymidine as a model compound for AZT.  One such alternative involves heating an alcohol in a reagent mixture of sodium cyanide, chlorotrimethyl silane, acetonitrile, sodium iodide, and dimethyl formamide under an inert atmosphere.

Development of a direct method to convert AZT into its 5′-cyano derivative

243rd National Meeting (2012)

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