4-Nitroaniline → 6-(5-Bromo-2-methyl-phenyl)-N4-(4-nitro-phenyl)-pyrimidine-2,4-diamine

HRID 28604

Reaction equation

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

Participants

Reactant 2

HCID 74754-Nitroaniline

HCID 860043412-Amino-4-chloro-6-(2-methyl-5-bromo-phenyl)-pyrimidine

Product 1

HCID 113840056-(5-Bromo-2-methyl-phenyl)-N*4*-(4-nitro-phenyl)-pyrimidine-2,4-diamineYield 74%

Procedure

Following the method described in Example 26, 4-(5-bromo-2-methyl-phenyl)-6-chloro-pyrimidin-2-ylamine and 4-nitro-phenylamine provided the title compound (74% yield). 1H NMR (CD3OD) δ 2.41 (s, 3H, CH3), 6.42 (s, 1H, Ar), 7.39 (d, 1H, J=8.0 Hz, Ar), 7.67-7.70 (m, 2H, Ar), 8.14 (d, 2H, J=9.0 Hz, Ar), 8.31-8.34 (m, 2H, Ar).

Sources & evidence

ORD record: ord-47733bb9bdf34592b169a13dab6e89bd
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Linked notes

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