反应详情

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.

1. concentrationMonitor loss of starting material by HPLC then concentrate
2. additionAdd two portions of toluene (50 mL)
3. customevaporate
4. filtrationFilter crude material
5. washwashing with 1:1 EtOAc/CH2Cl2
6. concentrationFinally, concentrate the filtrate and chromatograph on a silica column
7. washeluting with CH2Cl2/MeOH [0-10% MeOH gradient]