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

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Reaction Steps

This example illustrates a synthesis of 1-(10,11-Oxidoundecanyl)-3,7-dimethylxanthine (inventive compound no. 1594). 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 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 1 L of water and extracted with dichloromethane (5×200 mL). The organic extracts are combined, washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel (eluant: 20% hexane/dichloromethane) to yield 4.6 g (46.3% yield) 1-(10-Undecenyl)-3,7-dimethylxanthine (inventive compound no. 2501).

Provenance & Evidence