4-Chloroaniline → [6-(5-Chloro-2-methyl-phenyl)-2-methyl-pyrimidin-4-yl]-(4-chloro-phenyl)-amine

HRID 28561Notes

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

Participants

Reactant 2

HCID 78124-Chloroaniline

HCID 860043234-Chloro-6-(5-chloro-2-methyl-phenyl)-2-methyl-pyrimidine

Product 1

HCID 11336863[6-(5-Chloro-2-methyl-phenyl)-2-methyl-pyrimidin-4-yl]-(4-chloro-phenyl)-amineYield 97%

Procedure

Following the method described in Example 38 (alternate method), 4-chloro-6-(5-chloro-2-methyl-phenyl)-2-methyl-pyrimidine and 4-chloroaniline provided the title compound (97% yield). 1H NMR (DMSO-d6) δ 2.35 (s, 3H, CH3), 2.53 (s, 3H, CH3), 6.71 (s, 1H, Ar), 7.35-7.44 (m, 4H, Ar), 7.49 (d, 1H, J=2.2 Hz, Ar), 7.78 (d, 1H, J=8.8 Hz, Ar), 9.72 (s, 1H, NH).

Sources & evidence

ORD record: ord-03231f55cc36461b8a251e7fce83ce25
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Reaction notes

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