5-methylimidazolidine-2,4-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using (4-bromophenyl) [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (150 mg) described in Preparation Example 165 and 5-methylimidazolidine-2,4-dione (55 mg) and by the reaction and treatment in the same manner as in Example 1, the title compound (33 mg) was obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using (4-bromophenyl) [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (150 mg) described in Preparation Example 165 and 5-methylimidazolidine-2,4-dione (55 mg) and by the reaction and treatment in the same manner as in Example 1, the title compound (33 mg) was obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 5-methylimidazolidine-2,4-dione (1.00 g) and methyl iodide (0.57 mL) and by the reaction and treatment in the same manner as in Preparation Example 214, the title compound (1.66 g, containing DMF) was obtained. by the reaction and treatment in the same manner as in Preparation Example 214

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 5-methylimidazolidine-2,4-dione (1.00 g) and methyl iodide (0.57 mL) and by the reaction and treatment in the same manner as in Preparation Example 214, the title compound (1.66 g, containing DMF) was obtained. by the reaction and treatment in the same manner as in Preparation Example 214

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Methylimidazolidine-2,4-dione (1.00 g) was dissolved in N,N-dimethylformamide (20 mL), potassium tert-butoxide (1.08 g) and benzyl chloromethyl ether (1.32 mL) were added under ice-cooling, and the mixture was stirred at room temperature for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give the title compound (0.98 g). cooling the mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine the solvent was evaporated The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Methylimidazolidine-2,4-dione (1.00 g) was dissolved in N,N-dimethylformamide (20 mL), potassium tert-butoxide (1.08 g) and benzyl chloromethyl ether (1.32 mL) were added under ice-cooling, and the mixture was stirred at room temperature for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give the title compound (0.98 g). cooling the mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine the solvent was evaporated The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 5-methylimidazolidine-2,4-dione (2.00 g), 4-methoxybenzyl chloride (2.85 mL) and potassium carbonate (3.15 g) were added N,N-dimethylformamide (20 mL) and potassium iodide (0.29 g), and the mixture was stirred at 90° C. for 9 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was recrystallized from ethyl acetate/diisopropyl ether to give the title compound (2.82 g). The reaction mixture was cooled the mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine the solvent was evaporated The obtained residue was recrystallized from ethyl acetate/diisopropyl ether