Cesium carbonate → tert-Butyl (1-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)phenyl)ethyl)carbamate

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Reaction Conditions

Reaction Steps

A mixture of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.080 g, 0.24 mmol), tert-butyl 1-(4-aminophenyl)ethylcarbamate (0.067 g, 0.29 mmol), Xantphos (0.0057 g, 0.010 mmol) and Cs2CO3 (0.23 g, 0.71 mmol) in 1,4-dioxane (4 mL) was bubbled with nitrogen for 10 minutes. Palladium(II) acetate (0.0010 g, 0.0045 mmol) was added and the mixture was heated at 120° C. under microwave irradiation for 25 minutes. The mixture was partitioned between water and EtOAc. The layers were separated and the aqueous was extracted with EtOAc (2 times). The combined organic extracts were washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo to give the crude product. Purification by silica gel column chromatography (Combiflash Rf, 0-100% EtOAc in cyclohexane) gave the title compound 24 as a colourless oil (0.015 g, 12%). LCMS-C: rt 5.79 min; m/z 536 [M+H]+.

Provenance & Evidence