Phenethyl bromide → HCID 67143590, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of {(R)-2-[3-(2,6-difluoro-benzyl)-4-methyl-2,6-dioxo-5-piperazin-1-yl-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (2-2) (30 mg, 0.054 mmol) in DMF (1 mL) were added potassium carbonate (15 mg, 0.108 mmol), KI (1.3 mg, 0.0081 mmol), and (2-bromo-ethyl)-benzene (11.0 mg, 0.059 mmol) in the order, followed by stirring at 80° C. for 4 hrs. The solution was diluted in dichloromethane and washed with distilled water. After concentration of the organic layer thus formed, the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate/dichloromethane, 1/1/1) and dried in a vacuum to afford 25 mg of the compound as a colorless oil (yield 70%). 1H NMR (300 MHz, CDCl3) δ 1.35 (9H, s), 2.22 (2H, m), 2.44 (3H, s), 2.49 (2H, m), 2.63 (2H, t), 2.82 (2H, t), 2.88 (2H, m), 3.62 (2H, m), 4.04 (1H, dd), 4.25 (1H, t), 5.01 (1H, m), 5.01-5.36 (2H, dd), 5.84 (1H, m), 6.89 (2H, t), 7.17-7.40 (11H, m)

Provenance & Evidence