A benign and facile route to heterocycles, including triazoles and triazolopyrimidines, has been developed.  Continuous flow microreactor technology has been utilized to generate azides in situ and subsequently react them with cyanoacetamide in a [3+2] cycloaddition to yield a variety of useful building blocks. Given elevated concerns regarding the use of organic azides in macroscale synthesis, flow chemistry is a safe alternative to produce the reactive intermediates in a scalable fashion. By utilizing flow, the increased surface-to-volume ratio of the microreactor allows for efficient heating and mixing to take place, which can mitigate the risk of hazardous side reactions.  As a result, this highly efficient, yet safe method has allowed for the generation of a library of heterocycles that can be further elaborated to produce FDA-approved drugs, such as Brilinta�.

Facile and benign route to triazolopyrmidines using continuous flow chemistry

247th National Meeting (2014)

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