Thionyl Chloride → Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

Participants

Reaction Steps

To a round bottom flask equipped with a magnetic stir bar was added 4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.300 g, 1.3 mmol, 1.0 eq.), thionyl chloride (5 ml), and DMF (1 ml). The mixture was refluxed for 4 hour at which time the reaction was poured onto ice and NaHCO3. The aqueous layer was then extracted with ethyl acetate (2×). The organic layer was washed with water and brine, dried (Na2SO4), and concentrated in vacuo to give 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester as a brown solid (0.35 g 100% yield). MS (ESI, negative) for C9H8ClN3O2: 224 (M-H).

Provenance & Evidence