Veratrylamine → N-(3,4-dimethoxybenzyl)-N-[thieno[2,3-d]pyrimidin-6-ylmethylidene]amine
Reaction equation
[N:1]1[C:6]2[S:7][C:8]([CH:10]=O)=[CH:9][C:5]=2[CH:4]=[N:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:17][NH2:18]>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:17][N:18]=[CH:10][C:8]1[S:7][C:6]2[N:1]=[CH:2][N:3]=[CH:4][C:5]=2[CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Thieno[2,3-d]pyrimidine-6-carbaldehyde (intermediate 13) (40 mg), 3,4-dimethoxybenzylamine (0.04 ml) and 4 Å molecular sieves (150 mg) were heated at reflux in DCM (5 ml) for 3 hours under an inert atmosphere. The molecular sieves were removed by filtration and the solvent evaporated to afford the title compound as a pale yellow solid (76 mg, 100%);