Ammonium Chloride → 4-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-one

Participants

Reaction Steps

Add zinc (2 equiv; 12.12 mmol; 792 mg) to a suspension of 5,5-dibromo-4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (6.06 mmol; 1.98 g) in THF (20 mL) and add saturated ammonium chloride aqueous (3 mL) at 20° C. (exothermic). Stir 20 min then filter through Celite®, rinse with THF, wash the organic phase twice with saturated ammonium chloride. Extract combined aqueous layers four times with 100 mL 1:1 THF:EA, wash the combined organic phases with saturated ammonium chloride, dry over MgSO4, filter through silica gel plug, rinse with 1 L 5% MeOH/DCM and evaporate filtrates. Suspend crude solid in refluxing mixtures of DCM/EA and load onto 330 g of dry silica gel. Chromatograph with 0 to 2% MeOH/DCM to provide the title compound 3.89 g (22.93 mmol; 59%). MS (ES+): m/z=168 (M−H).

Provenance & Evidence