4-Chloroaniline → 6-[5-Bromo-2-(2-methoxy-ethoxy)-phenyl]-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28636Notes

Reaction equation

HRID 28636 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:6]([C:8]2[CH:13]=[C:12](Cl)[N:11]=[C:10]([NH2:15])[N:9]=2)[CH:7]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:6]([C:8]2[N:9]=[C:10]([NH2:15])[N:11]=[C:12]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)[CH:13]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 78124-ChloroanilineHCID 860043804-[5-Bromo-2-(2-methoxy-ethoxy)-phenyl)-6-chloro-pyrimidin-2-ylamine

Product 1

HCID 597882306-[5-Bromo-2-(2-methoxy-ethoxy)-phenyl]-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamineYield 79%

Procedure

Following the method described in Example 4, 4-[5-bromo-2-(2-methoxy-ethoxy)-phenyl)-6-chloro-pyrimidin-2-ylamine and 4-chloro-phenylamine provided the title compound (79% yield). 1H NMR (DMSO-d6) δ 3.26 (s, 3H, CH3), 3.71 (t, 2H, J=4.7 Hz, CH2), 4.19 (t, 2H, J=4.4 Hz, CH2), 6.36 (s, 2H, NH2), 6.74 (s, 1H, Ar), 7.11 (d, 1H, J=8.8 Hz, Ar), 7.31 (d, 2H, J=8.8 Hz, Ar), 7.52 (dd, 1H, J=8.8 Hz, J=2.6 Hz, Ar), 7.76 (d, 2H, J=8.7 Hz, Ar), 8.01 (d, 1H, J=2.6 Hz, Ar), 9.27 (s, 1H, NH).

Sources & evidence

ORD record
ord-3a116cf74fc646b9b2d1d599244a45f7
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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