Ammonia → 2-(3-methoxy-phenyl)-3H-thieno[3,2-d]pyrimidin-4-one
Reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=O.[NH3:21]>CO>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:11]2[NH:21][C:3](=[O:2])[C:5]3[S:6][CH:7]=[CH:8][C:9]=3[N:10]=2)[CH:17]=[CH:16][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(3-Methoxy-benzoylamino)-thiophene-2-carboxylic acid methyl ester, 24, (12.78 g) was added to methanol (200 mL) previously saturated with ammonia. The mixture was placed in a bomb reactor, and heated to 100° for 2 days. The solvent was then removed in vacuo and the resulting residue was suspended in isopropanol (250 mL); 2M sodium hydroxide solution was then added (83 mL), and the mixture was heated to reflux for 5 hours. The reaction mixture was then cooled and acidified to pH 1. 2-(3-methoxy-phenyl)-3H-thieno[3,2-d]pyrimidin-4-one, 25, (12.16 g) was collected as a white solid.