Bromide ion → Benzamidine

Participants

Reaction Steps

The key intermediate for pyrrolo[2,3-d]pyrimidines with phenoxymethylene, alkoxymethylene or oxime ether moieties at C-6 is the bromide 7, which is prepared in 6 steps from methyl cyanoacetate and chloroacetone (scheme 4). The monoalkylation product 2 is protected as 1,3-dioxolane, then the pyrimidine ring is formed by reaction with a benzamidine. Cyclization of the pyrrole ring occurs on reaction with aqueous HCl, and refluxing with POCl3 yields the chloride 5. Boc-protection of the pyrrole followed by radical bromination with NBS gives the bromide 7.

Provenance & Evidence