Allyl bromide → 4-(9-allyl-2-chloro-8-iodo-9H-purin-6-yl)morpholine

Participants

Reaction Conditions

Reaction Steps

4-(2-chloro-8-iodo-9H-purin-6-yl)morpholine (500 mg, 1.0 mmol) was stirred together with cesium carbonate (890 mg, 2.7 mmol) in DMF (4.2 mL) at ambient temperature for 10 minutes. Allyl bromide (0.36 mL, 4.1 mmol) was introduced and the reaction mixture was heated at 50° C. for 2 hr. The mixture was cooled to ambient temperature and diluted with brine and DCM and the layers separated. The aqueous phase was extracted into DCM (3×), dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford 4-(9-allyl-2-chloro-8-iodo-9H-purin-6-yl)morpholine as a white foam (480 mg, 90%). 1H NMR (500 MHz, DMSO) δ 5.94 (d, J=10.6 Hz, 2H), 5.76 (s, 1H), 5.19 (d, J=10.3 Hz, 2H), 4.79 (d, J=16.9 Hz, 2H), 4.69 (s, 2H), 3.73 (s, 4H). LC/MS (ESI+): m/z 406 (M+H)

Provenance & Evidence