Triethylamine → HCID 86712681, compound

Participants

Reaction Conditions

Reaction Steps

Zinc(II) chloride (1.0 M in Et2O; 3.30 mL, 3.30 mmol) was added to a solution of 2,4-dichloro-5-(trifluoromethyl)pyrimidine (0.658 g, 3.03 mmol) in 1:1 DCE/t-BuOH (20 mL) at 0° C. under nitrogen. After stirring for 1 hour at 0° C., a solution of tert-butyl 4-aminobenzyl(2-hydroxyethyl)carbamate (A70) (0.734 g, 2.75 mmol) in 1:1 DCE/t-BuOH (20 mL) was added followed by a solution of Et3N (0.423 mL, 3.03 mmol) in 1:1 DCE/t-BuOH (5 mL) at 0° C. The resulting mixture was vigorously stirred at 0° C. for 30 minutes, then at room temperature for 20 hours. The volatiles were evaporated in vacuo and the residue adsorbed onto silica gel then purified by column chromatography (CombiFlash Rf, 80 g SiO2 cartridge, 10-40% EtOAc in cyclohexane) to give the title compound A71 as a white solid (1.06 g, 85%); 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 7.59-7.52 (m, 3H), 7.28 (m, 2H), 4.49 (s, 2H), 3.74 (s, 2H), 3.43-3.20 (m, 3H), 1.50 (s, 9H). LCMS-B: rt 7.856 min; m/z 447 [M+H]+.

Provenance & Evidence