Ethanol → 5-Bromo2-(6-hexyloxypyridin-3-yl)pyrimidine

Participants

Reaction Steps

233 mmol of 2-hexyloxypyridine-5-boronic acid, 300 ml of ethanol, a solution of 466 mmol of sodium carbonate in 150 ml of water and 2.3 mmol of tetrakis(triphenylphosphine)palladium(0) are added to a solution of 233 mmol of 2,5-dibromopyrimidine in 600 ml of toluene. The mixture is heated at the boil until the reaction is complete. The organic phase is separated off, the aqueous phase is extracted with dichloromethane, and the combined organic extracts are dried using sodium sulfate. After the solvent has been removed in vacuo, the crude product is separated off by column chromatography on silica gel 60 using dichloromethane as eluent and is recrystallized from n-heptane, giving 31 g (40%) of a colorless solid. m.p. 103-106° C.

Provenance & Evidence