2-[(5-Dimethylaminomethyl-3-thienyl)methylthio]ethylamine → 5-Nitro-2-{2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamino}-4(3H)-pyrimidone
Reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:9][CH:8]=[C:7]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[CH:6]=1)[CH3:3].CS[C:17]1[N:22]=[C:21]([OH:23])[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1>C(O)C>[N+:24]([C:20]1[C:21](=[O:23])[NH:22][C:17]([NH:14][CH2:13][CH2:12][S:11][CH2:10][C:7]2[CH:6]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[S:9][CH:8]=2)=[N:18][CH:19]=1)([O-:26])=[O:25]Participants
4
Procedure
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.