1-Bromopropane → 2-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-(ethoxy)pyrimidine

Participants

Reaction Steps

A mixture of 1.2 g of sodium hydride (60-65 wt. %) and 150 ml of tetrahydrofuran was treated with 8.5 g of 2-[4-(5-hydroxy-1-pentyl)phenyl]-5-(ethoxy)pyrimidine while gassing with nitrogen, stirred for 5 hours, treated with 4 g of propyl bromide and subsequently stirred at room temperature overnight. The reaction mixture was treated with 500 ml of water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time, dried over magnesium sulfate, filtered and subsequently concentrated. Chromato- graphy of the residue on silica gel with hexane/ethyl acetate (vol. 9:1) and recrystallization from ethyl alcohol gave 7.5 g of pure 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-(ethoxy)pyrimidine.

Provenance & Evidence