Potassium Carbonate → 7-Benzyl-3-cyclopropylmethyl-1-propoxymethylxanthine

Participants

Reaction Steps

1.12 g (8.1 mmol) of potassium carbonate were added at 60° C. to a solution of 1.5 g (5.06 mmol) of 7-benzyl-3-cyclopropylmethylxanthine from stage a) in 60 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 722 μl (6.58 mmol) of propoxymethyl chloride were then added dropwise and the mixture was stirred at 80° C. for 4 hours. 12 ml of water and 5 ml of methanol were added and the mixture was stirred at 50° C. for 2 hours. 60 ml of water were then added again, the mixture was extracted three times using methyl tert-butyl ether, and 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