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Selective N-methylation of amides using (chloromethyl) dimethylchlorosilane / fluoride: Application to the large scale synthesis of a pyrimidone intermediate for Raltegravir

Raltegravir (free base) Selective N- v’s O- alkylation of an amide can be challenging and somewhat unpredictable- the outcome being highly dependent on the structure of the substrate. A good example of this is the N-methylated pyrimidone intermediate (5) en route to Merck’s antiretroviral drug Raltegravir.1 Direct methylation of amide (4) (Figure 1) using MeI gives significant

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