Cesium carbonate → tert-Butyl 4-(5-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino) pyridin-2-yl)piperidine-1-carboxylate

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Reaction Steps

A suspension of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.150 g, 0.446 mmol), Cs2CO3 (0.436 g, 1.34 mmol) and tert-butyl 4-(5-aminopyridin-2-yl)piperidine-1-carboxylate 19 (247 mg, 0.892 mmol) in 1,4-dioxane (3 mL) was sonicated for 10 minutes. Xantphos (10 mg, 18 μmol) and Pd(II) acetate (2.0 mg, 8.9 μmol) were added and the mixture was irradiated in the microwave at 120° C. for 20 minutes. The mixture was adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in cyclohexane) to give the title compound A19 as a yellow oil (79 mg, 31%). LCMS-C: rt 4.92 min; m/z 577.0 [M+H]+.

Provenance & Evidence