Cesium carbonate → tert-Butyl 4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)benzylcarbamate

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Reaction Conditions

Reaction Steps

A suspension of 2-(2-(2-(2-chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide (K6) (0.150 g, 0.518 mmol), 4-(N-Boc-aminomethyl)aniline (0.145 g, 0.621 mmol), Pd(OAc)2 (2.3 mg, 0.010 mmol), Cs2CO3 (0.506 g, 1.55 mmol) and Xantphos (12 mg, 0.021 mmol) in 1,4-dioxane (2 mL) was heated under microwave irradiation at 100° C. for 1.5 hours. The resulting mixture was filtered through a plug of silica gel, washing with 10% MeOH in DCM. The volatiles were removed in vacuo and the residue was adsorbed onto silica gel and the product purified using silica gel column chromatography (CombiFlash Rf, 12 g SiO2 cartridge, 0-5% MeOH in DCM) to give the title compound A114 as a white solid (0.043 g, 17%); 1H NMR (300 MHz, d4-MeOH) δ 8.07 (brs, 1H), 7.59 (brs, 2H), 7.19 (m, 6H), 4.19 (brs, 2H), 3.64 (brs, 2H), 3.11 (brs, 2H), 2.95-2.98 (m, 2H), 2.08 (brs, 3H), 1.46 (brs, 9H). LCMS-B: rt 6.636 min; m/z 476 [M+H]+.

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