Diethylamine → HCID 18924858, compound
Reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:6]2[C:11]([CH3:12])=[C:10]([CH3:13])[S:9][C:7]=2[N:8]=1.[CH2:24]([NH:26][CH2:27]C)C>ClCCl>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([C:5]2[C:6]3[C:11]([CH3:12])=[C:10]([CH3:13])[S:9][C:7]=3[N:8]=[C:3]([CH2:2][N:26]([CH3:27])[CH3:24])[N:4]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-chloromethyl-4-(3,4-dimethoxyphenyl)-5,6-dimethylthieno[2,3-d]pyrimidine (1.0 g), diethylamine (1.2 ml) and dichloromethane (30 ml) was stirred for 16 hours under reflux. The reaction mixture was concentrated under reduced pressure, which was dissolved in ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-methanol (5:1, v/v), was obtained 4-(3,4-dimethoxyphenyl)-5,6-dimethyl-2-(N,N-dimethylamino-methyl)thieno[2,3-d]pyrimidine (0.49 g, 44%). Recrystallization from isopropyl ether gave colorless prisms, m.p.118°-120° C.