4-Chloroaniline → 6-(5-Chloro-2-cyclohexylmethoxy-phenyl)-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28653Notes

Reaction equation

HRID 28653 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[O:15][CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:5]=[C:4]([NH2:23])[N:3]=1.[Cl:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1>>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:8]([C:6]2[N:5]=[C:4]([NH2:23])[N:3]=[C:2]([NH:29][C:28]3[CH:30]=[CH:31][C:25]([Cl:24])=[CH:26][CH:27]=3)[CH:7]=2)[CH:13]=1

Participants

3

Reactant 2

HCID 78124-ChloroanilineHCID 860043894-Chloro-6-(5-chloro-2-cyclohexylmethoxy-phenyl)-pyrimidin-2-ylamine

Product 1

HCID 597882656-(5-Chloro-2-cyclohexylmethoxy-phenyl)-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamineYield 98%

Procedure

Following the method described in Example 72, 4-chloro-6-(5-chloro-2-cyclohexylmethoxy-phenyl)-pyrimidin-2-yl-amine and 4-chloro-aniline provided the title compound (98% yield). 1H NMR (DMSO-d6) δ 1.15-1.19 (m, 4H, CH2) δ 1.65-1.73 (m, 6H, CH2), 3.89 (d, 2H, J=5.7 Hz, Ar), 6.49 (s, 1H, Ar), 7.27 (d, 1H, J=8.4 Hz, Ar), 7.46 (d, 2H, J=8.7 Hz, Ar), 7.61 (d, 2H, J=8.5 Hz, Ar), 7.82-7.85 (m, 2H, Ar).

Sources & evidence

ORD record
ord-a03b788da50b433cb0a2a7e2994b25af
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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