Adenine → 9-Methyladenine

Participants

Reaction Steps

A mixture of 43.2 g (0.23 mol) of adenine and 210 ml of 40% aqueous tetrabutylammonium hydroxide was stirred at room temperature for 30 minutes and 250 ml of methylene chloride was added. To this heterogenous mixture was added 40 ml (0.64 mol) of methyl iodide in 200 ml of methylene chloride. A further 450 ml of methylene chloride was added and the reaction was stirred vigorously for ten hours. The reaction was cooled to 10° and the liquid phase comprising methylene chloride and water was decanted from a milky precipitate which had formed. Methanol was added to the precipitate and the mixture warmed gently to 40°, cooled to 10° and the resulting granular solid filtered off. The solid was recrystallized from 350 ml of water to provide 20.9 g of 9-methyladenine.

Provenance & Evidence