Reaktion #309349

Reaktionsgleichung

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Selectfluor

1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

AcOH

→

title compound

Ausbeute 36.0%

4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine

Ausbeute 36.0%

Lösungsmittel

AcCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to rt
2. 2
   Einengenthe mixture was concentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in a solution of 50% DCM in EtOAc
4. 4
   Filtrationfiltered through a pad of silica gel which
5. 5
   Waschenwas thoroughly washed
6. 6
   EinengenThe filtrate was concentrated in vacuo
7. 7
   Sonstigethe residue was purified by silica gel chromatography
8. 8
   Wascheneluting with a gradient of 0 to 30% EtOAc in DCM

Vorschrift

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).

Quelle