Cesium carbonate → 4-(2-((5-Chloro-1-methyl-1H-pyrazol-4-yl)amino)-4-cyclobutoxy-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a degassed mixture of 4-(2-chloro-4-cyclobutoxy-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylbenzamide (1 equiv), 5-chloro-1-methyl-1H-pyrazol-4-amine hydrochloride (1 equiv) and cesium carbonate (5 equiv) in 1,4-dioxane (0.09 M) was added tris(dibenzylideneacetone)dipalladium(0) (0.1 equiv) and (dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine) (0.2 equiv). The reaction was stirred at 100° C. for 16 h. The reaction mixture was cooled to room temperature, and concentrated. The residue was purified by silica gel chromatography (0-5% MeOH in DCM) to afford the title compound (23% yield). MS (ESI) m/z 582.4 [M]+.

Provenance & Evidence