N,N'-Dimethylethylenediamine → 1-{5-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-4-methylimidazolidin-2-one

Participants

Reaction Steps

To a mixture of (6-bromopyridin-3-yl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (150 mg) described in Preparation Example 127, 1-benzoyl-5-methylimidazolidin-2-one (105 mg) described in Preparation Example 56, cesium carbonate (260 mg) and copper(I) iodide (38 mg) were added 1,4-dioxane (8 mL) and N,N′-dimethylethylenediamine (43 μL), and the mixture was stirred with heating under reflux for 18 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (68 mg) produced by debenzoylation that simultaneously proceeded during the reaction.

Provenance & Evidence