4-(Trifluoromethyl)aniline → 6-(3-Bromo-phenyl)-N*4*-(4-trifluoromethyl-phenyl)-pyrimidine-2,4-diamine

HRID 28626Notes

Reaction equation

HRID 28626 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=2)[N:5]=[C:4]([NH2:15])[N:3]=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>>[Br:14][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[C:4]([NH2:15])[N:3]=[C:2]([NH:22][C:21]3[CH:23]=[CH:24][C:18]([C:17]([F:16])([F:25])[F:26])=[CH:19][CH:20]=3)[CH:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 587333892-Pyrimidinamine,4-(3-bromophenyl)-6-chloro-

Product 1

HCID 597882646-(3-Bromo-phenyl)-N*4*-(4-trifluoromethyl-phenyl)-pyrimidine-2,4-diamineYield 30%

Procedure

Following the method described in Example 53, 4-chloro-6-(3-bromo-phenyl)-pyrimidin-2-ylamine and 4-trifluoromethylaniline provided the title compound (30% yield). 1H NMR (CD3OD) δ 6.50 (s, 1H, Ar), 7.25-7.35 (t, 1H, Ar), 7.4-7.6 (m, 4H, Ar) 7.88 (d, 1H, Ar), 7.90 (d, 1H, Ar) 7.96 (d, 2H, Ar), 8.10 (s, 1H, Ar).

Sources & evidence

ORD record
ord-23d96adfa30148e890ed5a7faaf56e6e
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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