tert-Butanol → Tert-butyl 1-(4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamate

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Reaction Steps

ZnCl2 (1.0 M in Et2O; 3.27 mL, 3.27 mmol) was added to a stirred solution of 2,4-dichloro-5-(trifluoromethyl)pyrimidine (620 mg, 2.86 mmol) in a 1:1 t-BuOH:DCE mixture (120 mL) at room temperature. After stirring for 20 minutes tert-butyl 1-(4-aminophenyl)ethylcarbamate (0.643 g, 2.72 mmol) (prepared according to Bioorganic and Medicinal Chemistry Letters, 14(7), 1751-1755; 2004) followed by Et3N (455 μL, 3.27 mmol) was added and the resulting mixture stirred at room temperature overnight. The volatiles were evaporated to dryness and the resulting residue purified by silica gel column chromatography (CombiFlash Rf, SiO2 cartridge, 0-10% EtOAc in cyclohexane) to give the title compound A63 (480 mg, 42%); 1H NMR (300 MHz, CDCl3) δ 8.57 (s, 1H), 7.56 (m, 1H), 7.56 (d, J=8.61 Hz, 2H), 7.33 (d, J=8.61 Hz, 2H), 4.81 (m, 2H), 1.46 (m, 12H). LCMS-B: rt 8.47 min; m/z 417 [M+H]+.

Provenance & Evidence