Methyl iodide → HCID 17876723, compound

Participants

Reaction Steps

To a solution of 1-(2,4-dimethoxybenzoylpiperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (100 mg, 2.53 mmol) from Example 35 in DMF (50 mL) was added Nail (16 mg of a 60% suspension in mineral oil, 0.40 mmol) followed by iodomethane (0.031 mL, 0.50 mmol). The reaction was stirred for 18 h at ambient temperature. More NaH (10 mg, 0.25 mmol) and iodomethane (0.031 mL, 0.50 mmol) were added and the reaction was stirred at ambient temperature for 24 h. The reaction was quenched by the addition of HOAc (0.2 mL) and the solvents were removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 90:10 EtOAc:hexanes as eluant. The title compound was obtained as an oil (45% yield). TLC: Rf =0.42 (97:3 CHCl3 :MeOH) HPLC (method A): retention time 8.53 min FAB MS: m/z 410 (M+ +H)

Provenance & Evidence