Methyl iodide → Xanthine

Participants

Reaction Conditions

Reaction Steps

60 g of 3-n-butyl-7-(5'-oxohexyl)-xanthine are added to a solution of 8 g of sodium hydroxide in 160 ml of a methanol/water mixture (1:1). 28 g of methyl iodide are dropwise added to the clear solution having a temperature of 40° C. and the mixture is stirred at 48° C. for 24 hours. After concentration under reduced pressure the residue is diluted with 300 ml of diethylether and the unreacted 3-(n-butyl)-7-(5'-oxohexyl)-xanthine is removed by shaking with 1 N sodium hydroxide. After neutralisation, drying, concentration under reduced pressure and distillation at 140° C. temperature of the mixture and 0.02 mmHg 48.5 g of 1-methyl-3-(n-butyl)-7-(5'-oxohexyl)-xanthine are obtained from the ether phase as a viscous oil (nD20 =1.5320; yield 77.2%, referred to reacted starting xanthine). Analysis: C16H24N4O3 =320.396

Provenance & Evidence