3-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine → 5-Nitro-2-[3-(3-piperidinomethylphenoxy)propylamino]-4(3H)-pyrimidone

Participants

Reaction Steps

A solution of 3-(3-piperidinomethylphenoxy)propylamine (8.20 g; 33.0 mmoles) and 2-methylthio-5-nitro-4-hydroxypyrimidine (6.20 g; 32.5 mmoles) [prepared according to the procedure described in U.S. Pat. No. 4,241,056] in 35 ml of ethanol was stirred at reflux temperature for 18 hours. The reaction mixture was evaporated under reduced pressure, and the residue was placed on 250 g of silica gel (230-400 mesh) and chromatographed by flash chromatography using a gradient elution of methanol-methylene chloride. The appropriate fractions were combined and evaporated, and the product was recrystallized from tetrahydrofuran to give the title compound, mp 161°-164° C.

Provenance & Evidence