Potassium Carbonate → 7-Benzyl-1-ethoxymethyl-3-propylxanthine

Participants

Reaction Conditions

Reaction Steps

1.71 g (12.0 mmol) of potassium carbonate were added to a hot solution of 2.2 g (7.7 mmol) of 7-benzyl-3-propylxanthine from stage a) in 60 ml of dimethylformamide at 60° C. and the mixture was stirred at 60° C. for 1 hour. 0.93 ml (10.0 mmol) of ethoxymethyl chloride was then added dropwise and the mixture was stirred at 80° C. for 4.5 hours. A further 0.5 ml (5.3 mmol) of ethoxymethyl chloride was then added and the mixture was again stirred for 6 hours. 12 ml of water and 5 ml of methanol were then added, the mixture was allowed to stand overnight, 60 ml of water were added again and the mixture was extracted three times using methyl tert-butyl ether. The combined organic phases were washed twice with water, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19.8/0.2).

Provenance & Evidence