2-Ethylbenzimidazole → HCID 59605258, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (2.5 g, 5.52 mmol), 2-ethylbenzimidazole (968 mg, 6.62 mmol), tris(dibenzylideneacetone)dipalladium (126 mg, 0.14 mmol), XPhos (263 mg, 0.55 mmol) and K3PO4 (2.34 g, 11.04 mmol) in dioxane (50 mL) was purged with N2 then heated at 100° C. for 6 h before further tris(dibenzylideneacetone)dipalladium (126 mg, 0.14 mmol) and XPhos (263 mg, 0.55 mmol) were added. The resulting mixture was heated at 100° C. for 18 h then diluted with 2-methyl THF and filtered through Celite®. The filtrate was washed with H2O and brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, EtOAc:cyclohexane, 40-100%) affording 4-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (2.6 g, 84%). LCMS (method H): RT 2.99 min, [M+H]+ 563.4

Provenance & Evidence