Dimethylformamide → 2-[(4,6-Dimethoxypyrimidin-2-yl)oxy]naphthalene-1-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

8.6 g (0.05 mol) of 2-hydroxynaphthalene-1-aldehyde are introduced into 50 ml of dry dimethylformamide and admixed by stirring, at 0°-5° C., with 1.5 g (0.05 mol) of 80% strength sodium hydride added a little at a time. 10.9 g (0.05 mol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine are then added at room temperature, and the mixture is heated to 90° C. and stirred at that temperature for 6 hours. The solution thus obtained is poured into water. The aqueous mixture is extracted with methylene chloride, carefully washed with water, dried over sodium sulfate and concentrated under reduced pressure. The crude product is further purified by stirring out with cold toluene, leaving 7.4 g of 2-(4,6-dimethoxypyrimidin-2-yloxy)naphthalene-1-aldehyde of m.p. 123°-125° C.

Provenance & Evidence