Allyl bromide → 5-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

Participants

Reaction Steps

To a room temperature solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.2 g, 7.8 mmol,) and allyl bromide in 40 mL of DMF was added 60% sodium hydride (625 mg, 15.6 mmol, 2 equiv.) in several portions. After 20 minutes, the reaction was quenched with water and extracted with EtOAc. The combined organics were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (20% EtOAc/hexanes) to provide 1.3 g (88%) of 5-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine as a yellow oil which was used without further purification.

Provenance & Evidence