4-(Trifluoromethyl)aniline → 2,4-Pyrimidinediamine, 6-(5-chloro-2-methylphenyl)-N4-(4-(trifluoromethyl)phenyl)-

HRID 28542

Reaction equation

HRID 28542 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH2:16])[N:3]=1.[F:17][C:18]([F:27])([F:26])[C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1>>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([CH3:15])=[C:8]([C:6]2[N:5]=[C:4]([NH2:16])[N:3]=[C:2]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([C:18]([F:17])([F:26])[F:27])=[CH:20][CH:21]=3)[CH:7]=2)[CH:13]=1

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 860043474-Chloro-6-(5-chloro-2-methylphenyl)pyrimidin-2-yl-amine

Product 1

HCID 100225822,4-Pyrimidinediamine, 6-(5-chloro-2-methylphenyl)-N4-(4-(trifluoromethyl)phenyl)-Yield 46%

Procedure

Following the method described in Example 26, 4-chloro-6-(5-chloro-2-methyl-phenyl)-pyrimidin-2-yl-amine and 4-trifluoromethyl-phenylamine provided the title compound (46% yield). 1H NMR (DMSO-d6) δ 2.36 (s, 3H, CH3), 6.17 (s, 1H, Ar), 6.54 (s, 2H, NH2), 7.32 (d, 1H, J=8.3 Hz, Ar), 7.38 (dd, 1H, J=8.1 Hz, J—2.3 Hz, Ar), 7.43 (d, 1H, J=2.1 Hz, Ar), 7.61 (d, 2H, J=8.7 Hz, Ar), 8.00 (d, 2H, J=8.5 Hz, Ar), 9.63 (s, 1H, NH).

Sources & evidence

ORD record
ord-6c72a0947b534124b7eeeaec8aa2d13c
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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