2-[(5-Dimethylaminomethyl-3-thienyl)methylthio]ethylamine → 5-Nitro-2-{2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamino}-4(3H)-pyrimidone

Participants

Reaction Steps

A mixture containing 2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamine (2.88 g; 12.5 mmoles) and 2-methylthio-5-nitro-4-hydroxypyrimidine (2.33 g; 12.44 mmoles) in 10 ml of ethanol was heated at reflux temperature for 13 hours. The reaction mixture was evaporated under reduced pressure, and the residue was placed on 150 g of silica gel and chromatographed by flash chromatography using a gradient elution of methanol-methylene chloride. The appropriate fractions gave 2.92 g of product which was recrystallized from tetrahydrofuran to give the title compound, mp 150°-153° C.

Provenance & Evidence