Water → 1-(6-Hydroxyhexyl)-3,7-dimethylxanthine

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Reaction Steps

This example is a synthesis for inventive compound no. 1527 (see above for chemical name and structure). A mixture of theobromine (1.0 g, 5.5 mmol, available from Sigma) and a solution (20 ml) of 50% sodium hydride in oil (264 mg, 5.5 mmol) in dimethylsulfoxide was stirred for 50 minutes, followed by addition of 6-bromo-1-hexanol (1.0 g, 5.5 mmol, available from Aldrich). After stirring for 18 hours, the solution was treated with 50 ml of water and then extracted with two 25 ml aliquots of hexanes. The aqueous phase was extracted with three 35 ml aliquots of 25% ethanol-dichloromethane. The combined ethanol-dichloromethane extracts were dried over magnesium sulfate and then the solvents were evaporated under vacuum. The remaining dimethylsulfoxide was removed by distillation under full pump vacuum, producing 1.4 g of a white powder, 1-(6-hydroxyhexyl)-3,7-dimethylxanthine (5.0 mmol, 91% yield).

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