Tetrahydrofuran → HCID 59605394, compound

Participants

Reaction Steps

To a solution of (9-ethyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methanol (3 g, 7.65 mmol) in tetrahydrofuran (150 mL, 1800 mmol) was added phosphorus tribromide (1.44 mL, 15.3 mmol;) dropwise. The mixture was stirred for 2 hrs until LC/MS showed the reaction was complete. The reaction was quenched with MeOH and extracted with Ethyl acetate and water. The organic layer was collected, dried with Magnesium sulfate, filtered and concentrated to give a crude orange oil. The oil was purified by flash chromatography to give 2.6 g of 4-(8-(bromomethyl)-9-ethyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-9H-purin-6-yl)morpholine as an orange solid, of which 50 mg was reacted with 2-(piperidin-4-yl)propan-2-ol via Gen Procedure E to give 34.6 mg 236 following reverse phase purification. MS (Q1) 519.3 (M)+

Provenance & Evidence