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

HRID 28645Notes

Reaction equation

HRID 28645 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]1[CH:21]=[C:20](Cl)[N:19]=[C:18]([NH2:23])[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]1[N:17]=[C:18]([NH2:23])[N:19]=[C:20]([NH:29][C:28]2[CH:30]=[CH:31][C:25]([Cl:24])=[CH:26][CH:27]=2)[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 78124-ChloroanilineHCID 860043874-(2-Benzyloxy-5-chloro-phenyl)-6-chloro-pyrimidin-2-ylamine

Product 1

HCID 597882346-(2-Benzyloxy-5-chloro-phenyl)-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamineYield 98%

Procedure

Following the method described in Example 72, 4-(2-benzyloxy-5-chloro-phenyl)-6-chloro-pyrimidin-2-ylamine and 4-chloro-aniline provided the title compound (98% yield). 1H NMR (CD3OD) δ 5.26 (s, 2H, CH2), 6.44 (s, 1H, Ar), 7.21 (d, 1H, J=8.8 Hz, Ar), 7.33-7.36 (m, 2H, Ar), 7.38-7.43 (m, 4H, Ar), 7.45 (d, 1H, J=8.8 Hz, Ar), 7.58-7.61 (m, 2H, Ar), 7.80-7.82 (m, 2H, Ar).

Sources & evidence

ORD record
ord-a1f6aae8fc4a46109386478bc68ee302
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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