2,4-Dichloro-1,3,5-triazine → (4-Chloro-[1,3,5]triazin-2-yl)-[4-methoxy-3-(2-methoxy-ethoxy)-phenyl]amine

HRID 983446Notes

Reaction equation

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:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=1[O:27][CH2:28][CH2:29][O:30][CH3:31]>CN(C=O)C.CCOC(C)=O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[C:21]([O:27][CH2:28][CH2:29][O:30][CH3:31])[CH:22]=2)[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,4-Dichloro-1,3,5-triazine (89.1 mg, 0.5944 mmol) was dissolved in DMF (0.5 ml) and cooled to 0° C. To this solution were added DIEA (104 μl), 4-methoxy-3-(2-methoxy-ethoxy)phenylamine (TFA salt)(264 mg, ˜0.59 mmol) and DIEA (208 μl) in DMF (1 ml). The reaction mixture was kept at 0° C. for 15 to 30 min and then at RT for 15 min to 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, to give (4-chloro-[1,3,5]triazin-2-yl)-[4-methoxy-3-(2-methoxy-ethoxy)-phenyl]amine.

Workup

waitat RT for 15 min to 2 h
washwashed with brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-5260589d11c646f19ccd14bb6a3817b8
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864255B2

Reaction notes

Loading…