Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[NH2:23]>CN(C=O)C.CCOC(C)=O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:23][C:22]2[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:20]([O:19][CH3:18])[CH:21]=2)[N:7]=12,4-Dichloro-1,3,5-triazine (1.054 g, 7.028 mmol) is dissolved in DMF (5 ml) and cooled to 0° C. To this solution, DIEA (1.225 ml, 7.028 mmol) and 3,4,5-trimethoxyaniline (1.185 g, 6.47 mmol) are added. The reaction mixture is kept at 0° C. for 15 to 30 min and at RT for about 2 h. The reaction mixture is diluted with EtOAc and washed with brine. The organic layer is dried over Na2SO41 filtered, and evaporated in vacuo. The residue is added to CH2Cl2 and the resulting white precipitate is filtered and dried under reduced pressure to give (4-chloro-[1,3,5]triazin-2-yl)-(3,4,5-trimethoxy-phenyl)amine.
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