1-Bromooctane → 2-(2,3-Difluoro-4-octyloxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine

Participants

Reaction Steps

A solution of 2.4 mmol of 2-(2,3-difluoro-4-hydroxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine in 10 ml of DMF is added dropwise at room temperature and under a protective gas to a suspension of 2.7 mmol of sodium hydride (80 percent in mineral oil) in 5 ml of dry DMF. The mixture is stirred for a further 30 minutes, and 2.7 mmol of 1-bromooctane, dissolved in 10 ml of DMF, are then added slowly. The reaction mixture is stirred at room temperature for 20 hours and introduced into 100 ml of ice/water, the mixture is extracted a number of times with dichloromethane, and the combined organic extracts are washed with sat. sodium chloride solution and dried using magnesium sulfate. After the solvent has been removed in vacuo, the crude product is chromatographed on silica gel 60 using dichloromethane/ethyl acetate 20:1 (v/v) as eluent and recrystallized from acetonitrile, giving 0.77 g (61%) of colorless crystals, X 89 S3 73.5 SC 164 SA 167 I.

Provenance & Evidence