8-Chloro-10-(trifluoromethyl)pyrimido[5,4-b]quinolin-4(3H)-one → 10-(4-Bromobenzyl)-8-chloro-10-(trifluoromethyl)-5,10-dihydropyrimido[5,4-b]quinolin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 7 (200 mg, 0.667 mmol) in THF (4 mL) at −40° C. was added 4-bromobenzyl magnesium bromide (0.25 M in Et2O, 13.3 mL, 3.34 mmol). The reaction was warmed slowly to 0° C. over 2 h. After stirring an additional 2 h, the reaction was quenched with H2O (20 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated. Chromatography (SiO2, 40 to 50% EtOAc-hexane) afforded the desired product as a viscous orange oil (134 mg, 43%). ESI-MS m/z 470.2 (M++H, C19H12BrClF3N3O).

Provenance & Evidence