Methyl iodide → HCID 178487818, compound

Participants

Reaction Conditions

Reaction Steps

Sodium carbonate (405 mg, 3.82 mmol, 3.5 eq) is added at −5° C. to a stirred solution of 2-[trans-4-(6-methoxy-2-oxo-2,3-dihydro-1H-4-oxa-1,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-isoindole-1,3-dione (500 mg, 1.09 mmol, 1.0 eq) in N,N-dimethylformamide (30 mL), followed by iodomethane (408 μL, 6.55 mmol, 6.0 eq). After 14 hours stirring at −5° C., solvent is removed and the residue is extracted with ethyl acetate (3×100 mL) and water (100 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 2-[trans-4-(6-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-4-oxa-1,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-isoindole-1,3-dione as a light red semisolid (420 mg, 81% yield).

Provenance & Evidence