2,4-Bis(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine → 2-Methylsulfonyl-4-(2-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750870Notes

Reaction equation

HRID 750870 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[C:9](S(C)(=O)=O)[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[N:6]=1)(=[O:4])=[O:3].C([Li])CCC.[OH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1>>[CH3:1][S:2]([C:5]1[N:10]=[C:9]([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[N:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 597538832,4-Bis(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine2×HCID 178418339ButyllithiumHCID 178516071HCID 178516071, compound

Product 1

HCID 104138842-Methylsulfonyl-4-(2-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Procedure

2,4-Bis(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Reference Example 5 (200 mg, 0.41 mmol) was reacted with 1.0 equivalent of n-butyl lithium and 1.1 equivalent of 2-hydroxypyridine by the procedure described in Example 86 to afford the title compound: 1H-NMR 400 MHz (CDCl3): δ 3.22 (s, 3H), 7.15-7.33 (m, 8H), 7.38 (d, J=2 Hz, 1H), 7.85-7.90 (m, 1H), 8.30-8.42 (m, 1H).

Sources & evidence

ORD record
ord-f03860b9eea44771a59db0e357efa944
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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