Xanthine → 1,3-Dimethyl-7-(6-hydroxyhexyl)-xanthine

Participants

Reaction Steps

1,3-dimethyl-7-(6-bromohexyl)-xanthine is refluxed overnight with a sixfold molar excess of potassium acetate with the addition of catalytic quantities, such as 2 mol percent, referred to the xanthine, of potassium iodide in a mixture of 5 ml of acetic anhydride and 200 ml of glacial acetic acid. The solvent is evaporated in vacuo. The residue is dissolved in water and the pH of the solution is adjusted to a value of 7 with 4N sodium hydroxide. The solution is then extracted with chloroform. The isolated 1,3-dimethyl-7-(acetoxyhexyl)-xanthine is subsequently hydrolysed to the corresponding hydroxyalkyl compound by boiling with 5% sulfuric acid.

Provenance & Evidence