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

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Reaction Steps

Combine 4-Chloropyrrolo[2,3-d]pyrimidine (2.985 g, 19.40 mmol), [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate)] (Selectfluoro) (10.523 g, 29.704 mmol)], acetonitrile (200 mL), and acetic acid (40 mL) and heat to 70° C. for 24 hours. Monitor loss of starting material by HPLC then concentrate. Add two portions of toluene (50 mL) and evaporate. Filter crude material thru a pad of celite, washing with 1:1 EtOAc/CH2Cl2. Finally, concentrate the filtrate and chromatograph on a silica column eluting with CH2Cl2/MeOH [0-10% MeOH gradient]. Check fractions by MS and combine product fractions to provide 1.931 g (58%) of 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine.

Provenance & Evidence