Acetic Acid → 4-Chloro-5-fluoro-7H-pyrrolo(2,3-d)pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3.00 g, 19.5 mmol) in AcCN (148 mL) was added Selectfluor™ (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)), 10.4 g, 29.4 mmol) and AcOH (29.8 mL, 524 mmol), and then the mixture was allowed to stir for 26 hrs at 70° C. under an atmosphere of nitrogen. After cooling to rt, the mixture was concentrated in vacuo and the mixture was co-evaporated with dry toluene (2×30 mL). The residue was dissolved in a solution of 50% DCM in EtOAc and filtered through a pad of silica gel which was thoroughly washed. The filtrate was concentrated in vacuo, the residue was purified by silica gel chromatography eluting with a gradient of 0 to 30% EtOAc in DCM to afford the title compound as a light brown solid (1.22 g, 36%). LC/MS: Rt=1.51 min, ES+ 243 (AA standard).

Provenance & Evidence