Chloroacetaldehyde → 7-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Participants

Reaction Steps

In some embodiments, condensation of 2,6-diamino-1,2-dihydro[3H]pyrimidin-4-one with chloroacetaldehyde, followed by treatment with phosphorus oxychloride and anime protection with benzyl bromide provides 7-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine. In some embodiments, this is coupled with optionally substituted (R1, R2, R3, R4) para-bromo phenol or thiol (T=O, S) or para-bromoaniline (T=NH). In some embodiments, conversion of amine to fluoro is achieved by treatment with HF-pyridine, and then coupled with para-V-aniline. In some embodiments, benzyl deprotection is achieved by treatment with aluminum chloride to give the desired compound.

Provenance & Evidence