Raltegravir → 4-Fluorobenzylamine

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Reaction Steps

Among the advantages of the novel route of synthesis of raltegravir is the regioselective methylation of N-(4-fluorobenzyl)-2-(2-(5-methyl-1,3,4-oxadiazole-2-carboxamido)propan-2-yl)-1,6-dihydro-5-hydroxy-6-oxopyrimidine-4-carboxamide (VI) obtained by amidation of methyl-2-(2-(5-methyl-1,3,4-oxadiazole-2-carboxamido)propan-2-yl)-1,6-dihydro-5-hydroxy-6-oxopyrimidine-4-carboxylate (Va) with p-fluorobenzyl amine. The methylation reaction provides regioselectivity of more than 99% as against methylation of oxygen at 6th position, thereby resulting in a higher yield of more than 90%. The yield for the methylation reaction is in the range of 88 to 90%.

Provenance & Evidence