Pyridine → 1,3-Dibenzyl-5-(3-methyl-1-oxobutyl)barbituric acid

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Reaction Conditions

Reaction Steps

To a solution of 1,3-dibenzyl barbituric acid 265 mg (0.859 mmol) in dry dichloromethane 2.0 mL under a nitrogen atmosphere, added was pyridine 1.0 mL (12 mmol) and stirred at 0° C. Added was isovaleryl chloride 104 mg (0.858 mmol, 1.00 equivalent) in dichloromethane 1.0 mL to the solution slowly during a period of 20 minutes, then stirred at room temperature for 3 hours. Added was dichloromethane 50 mL and washed the organic layer with 2 M hydrochloric acid and saturated brine, and dried over sodium sulfate. Purified was the crude product 351 mg, after removal of the solvent under the reduced pressure, by column chromatography (silica gel, eluted with dichloromethane). It obtained 1,3-dibenzyl-5-(3-methyl-1-oxobutyl)barbituric acid 299 mg as colorless viscous oil at first, and in 2 days it turned white plates (88.7% yield).

Provenance & Evidence