Thymine → 1,5-Dimethyl-2,4(1H,3H)-pyrimidinedione

Participants

Reaction Conditions

Reaction Steps

Thymine (2.0 g, 16 mmol), hexamethyl-disilazane (32 mL) and trimethyl silylchloride (4.1 mL) were added in 100 mL mad apple-type flask with a magnetic stirrer and allowed to stir for 17 hr. at 140° C. until the reaction solution became transparent. After the reaction solution was cooled to 60° C., the solution was added with methyl-iodide (10 mL) and was allowed to stir for 29 hr. at 60° C. Then, the reaction solution was added with 6 N aqueous acetic acid solution (6 mL×10) and subjected to evaporation under reduced pressure. The residues were dissolved by the addition of 2-propanol and insolubles were filtered out. The filtrate was added with ethanol-water mixture. The object was recrystallized in ethanol-water mixture to give white solids (1.6 g, yield, 72%).

Provenance & Evidence