Water → 1-(10-Undecenyl)-3,7-dimethylxanthine

Participants

Reaction Conditions

Reaction Steps

This example is a method of synthesis for inventive compound no. 3537. Sodium hydride (95%, 1.26 g, 50 mmol) was added to a solution of theobromine (7.2 g, 40 mmol) in dimethylsulfoxide (300 ml). After 20 minutes of stirring, undecenylmesylate (7.95 g, 30 mmol) was added and the resulting mixture stirred for 12 hours at room temperature. The reaction was warmed to 70-80° C. and stirred for 4 hours. The reaction mixture was then poured into a separatory funnel containing water (1 L) and extracted with five 200 ml aliquots of dichloromethane. The organic extracts were combined, washed with water (100 ml) and brine (100 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, resulting in a crude product, which was further purified by flash chromatography over silica gel using a 20% hexane/dichloromethane eluant producing 4.6 g of 1-(10-undecenyl)-3,7-dimethylxanthine (46.3% yield).

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