4-(bromomethyl)cyclopentene

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

Procedure: 48 mg of 60% sodium hydride (1.20 mmol) was slowly added to 0.28 g of 5-ethyl-6-(α-cyano-3,5-dimethylbenzyl)-2,4-pyrimidinedione (1.0 mmol) dissolved in 10 ml of dimethyl formamide, and the mixture was stirred at room temperature for one hour. Then, 0.32 g of (cyclopent-3-en-1-yl)methyl bromide (2.0 mmol) was added to the resulting mixture and stirred at the temperature of 50˜60° C. for 48 hours with injection of oxygen. After cooling, 20 ml of distilled water was added to the resulting product, and extracted with 20 ml of ethyl acetate (2×). The obtained extract was dried with anhydrous magnesium sulfate and concentrated under the reduced pressure. Then, the concentrated residue was separated and purified with column chromatography (hexane:ethyl acetate=2:1) to obtain 0.23 g of the titled compound as a white solid. After cooling extracted with 20 ml of ethyl acetate (2×) The obtained extract was dried with anhydrous magnesium sulfate concentrated under the reduced pressure Then, the concentrated residue was separated purified with column chromatography (hexane:ethyl acetate=2:1)

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

Procedure: 48 mg of 60% sodium hydride (1.20 mmol) was slowly added to 0.28 g of 5-ethyl-6-(α-cyano-3,5-dimethylbenzyl)-2,4-pyrimidinedione (1.0 mmol) dissolved in 10 ml of dimethyl formamide, and the mixture was stirred at room temperature for one hour. Then, 0.32 g of (cyclopent-3-en-1-yl)methyl bromide (2.0 mmol) was added to the resulting mixture and stirred at the temperature of 50˜60° C. for 48 hours with injection of oxygen. After cooling, 20 ml of distilled water was added to the resulting product, and extracted with 20 ml of ethyl acetate (2×). The obtained extract was dried with anhydrous magnesium sulfate and concentrated under the reduced pressure. Then, the concentrated residue was separated and purified with column chromatography (hexane:ethyl acetate=2:1) to obtain 0.23 g of the titled compound as a white solid. After cooling extracted with 20 ml of ethyl acetate (2×) The obtained extract was dried with anhydrous magnesium sulfate concentrated under the reduced pressure Then, the concentrated residue was separated purified with column chromatography (hexane:ethyl acetate=2:1)