1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 9-Cyclopentyl-2-((5-((3R)-3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-2-pyridinyl)amino)-8-methyl-8,9-dihydro-7H-pyrido[3',2':4,5]pyrrolo[2,3-d]-pyrimidin-7-one

Participants

Reaction Conditions

Reaction Steps

A 10 mL reaction vessel was charged with compound 273 (55 mg, 193 μmol), (R)-5-(3-(t-butyldimethylsilyloxy)pyrrolidin-1-yl)-2-chloropyridine (60.3 mg, 193 μmol), tris(dibenzylideneacetone)dipalladium (0) (13 mg, 14 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (17 mg, 29 μmol), and sodium t-butoxide (22 mg, 231 μmol) in 2 mL dry dioxane. The reaction was purged with argon and heated with microwave energy (300 W) for 2 hours at 120° C. The resulting solution was taken up in ethyl acetate (40 mL) and washed with water (30 mL), and brine (30 mL). The organics were dried (MgSO4) and evaporated to give a brown oil. Silica gel chromatography (gradient elution hexanes+2.5% TEA/0-50% ethyl acetate+2.5% TEA) afforded compound 276 as a yellow solid (53 mg, 49%).

Provenance & Evidence