4-Chloroaniline → 6-[5-Bromo-2-(3-dimethylamino-propoxy)-phenyl]-N4-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28647Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[C:6]([C:8]2[CH:13]=[C:12](Cl)[N:11]=[C:10]([NH2:15])[N:9]=2)[CH:7]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[C:6]([C:8]2[N:9]=[C:10]([NH2:15])[N:11]=[C:12]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=3)[CH:13]=2)[CH:7]=1

Participants

Reactant 2

HCID 78124-Chloroaniline

HCID 865946054-[5-Bromo-2-(3-dimethylamino-propoxy)-phenyl]-6-chloro-pyrimidin-2-ylamine

Product 1

HCID 426072196-[5-Bromo-2-(3-dimethylamino-propoxy)-phenyl]-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamineYield 55%

Procedure

Following the method described in Example 4, 4-[5-bromo-2-(3-dimethylamino-propoxy)-phenyl]-6-chloro-pyrimidin-2-ylamine and 4-chloro-phenylamine provided the title compound (55% yield) as its hydrochloride salt. 1H NMR (CD3OD) δ 2.28-2.32 (m, 2H, CH2), 2.92 (s, 6H, CH3), 3.28-3.36 (m, 2H, CH2), 4.25 (m, 2H, CH2), 6.51 (s, 1H, Ar), 7.20-7.22 (m, 1H, Ar), 7.41-7.43 (m, 2H, Ar), 7.73-7.76 (m, 2H, Ar), 7.85-7.86 (m, 2H, Ar).

Sources & evidence

ORD record: ord-e2d766674a8341abb721ef195d996345
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Reaction notes

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