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) was 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) were added. The reaction mixture was kept at 0° C. for 15 to 30 min and at RT for 2 h. The reaction mixture was diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was added to CH2Cl2 and the resulting white precipitate was filtered and dried under reduced pressure to give (4-chloro-[1,3,5]triazin-2-yl)-(3,4,5-trimethoxy-phenyl)amine: MS m/z=279 [M−Cl+OH2]+. Calc'd for C12H13ClN4O3: 296.
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