Potassium Carbonate → 7-Benzyl-1-(4-chlorophenoxymethyl)-3-methylxanthine

Participants

Reaction Steps

2.59 g (19.0 mmol) of potassium carbonate were added at 60° C. to a suspension of 3.0 g (12.0 mmol) of 7-benzyl-3-methylxanthine (prepared according to Example 1a) in 50 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 2.69 g (15.0 mmol) of 4-chlorophenoxymethyl chloride were then added dropwise and the mixture was stirred at 80° C. for 8 hours. The crude mixture was then filtered, the filtrate was concentrated under reduced pressure, the residue was taken up in dichloromethane, and the solution was washed once with 1 N sodium hydroxide solution and twice with water. The organic phases were 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) Yield: 4.15 g (87% of theory); melting point: 96° C.

Provenance & Evidence