Methyl iodide → HCID 19357218, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of urea 1 (remaining half of crude product prepared above) in 1 mL of dry DMF at 0° C. was added NaH (14 mg, 60% dispersion in mineral oil). After 15 minutes, iodomethane (0.029 mL) was added dropwise. The reaction was stirred at 0° C. for four hours, then poured into EtOAc/hexane (2:1) and water, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide a purple oil. This material was purified by silica gel chromatography (2-5% MeOH/CH2Cl2), taken up in CH2Cl2 and treated with 1 M HCl/ether solution, and concentrated in vacuo. The product hydrochloride 8 (22 mg) was isolated as a yellow solid.

Provenance & Evidence