Water → 1-(8-Nonenyl)-3,7-dimethylxanthine

Participants

Reaction Conditions

Reaction Steps

Theobromine (1.98 g, 11 mmol) was added to a suspension of NaH (600 mg of a 50% mineral oil slurry, 12 mmol) in DMSO (15 ml). After 15 min, 9-methanesulfonyl-1-nonene (2.25 g, 11 mmol) was added and the reaction mixture was stirred for 6 days at 25° C. The reaction mixture was poured into 60 ml of water and extracted with dichloromethane (3×50 ml). The organic portions were combined, dried with magnesium sulfate, and evaporated to give a dark oil. Chromatography (silica, ethyl acetate) gave 1-(8-nonenyl)-3,7-dimethylxanthine (CT1550) as a colorless oil (810 mg, 26% yield).

Provenance & Evidence