4-Chloroaniline → 6-[5-Bromo-2-(2-morpholin4-yl-ethoxy)-phenyl]-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28642Notes

Reaction equation

HRID 28642 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[C:6]([C:8]2[CH:13]=[C:12](Cl)[N:11]=[C:10]([NH2:15])[N:9]=2)[CH:7]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[C:6]([C:8]2[N:9]=[C:10]([NH2:15])[N:11]=[C:12]([NH:32][C:29]3[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=3)[CH:13]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 78124-ChloroanilineHCID 865946044-[5-Bromo-2-(2-morpholin-4-yl-ethoxy)-phenyl)-6-chloro-pyrimidin-2-ylamine

Product 1

HCID 597882526-[5-Bromo-2-(2-morpholin4-yl-ethoxy)-phenyl]-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamineYield 83%

Procedure

Following the method described in Example 4, 4-[5-bromo-2-(2-morpholin-4-yl-ethoxy)-phenyl)-6-chloro-pyrimidin-2-ylamine and 4-chloro-phenylamine provided the title compound (83% yield). 1H NMR (CDCl3) δ 2.47 (m, 4H, 2CH2), 2.68 (t, 2H, J=5.6 Hz, CH2), 3.67 (m, 4H, 2CH2), 4.09 (t, 2H, J=5.7 Hz, CH2), 4.95 (s, 2H, NH2), 6.72-6.84 (m, 3H, Ar), 7.28-7.33 (m, 2H, Ar), 7.42-7.45 (m, 1H, Ar), 7.99 (s, 1H, Ar).

Sources & evidence

ORD record
ord-f829c1bf944445bbbe948b6553952c4c
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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