Sodium hydride → 2,4-Bis-(4-pyridyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750861Notes

Reaction equation

HRID 750861 reaction equation
CS([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)=O.[H-].[Na+].[OH:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1>>[N:36]1[CH:37]=[CH:38][C:33]([O:32][C:5]2[N:10]=[C:9]([O:32][C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[C:8]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[C:7]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:6]=2)=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 597538832,4-Bis(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine2×HCID 178418642HCID 178418642, compound

Product 1

HCID 117564852,4-Bis-(4-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 (500 mg, 1.02 mmol) was reacted with 1.1 equivalents each of sodium hydride (60% in oil, 45 mg, 1.12 mmol) and 4-hydroxy-pyridine (106.4 mg, 1.12 mmol) by the general procedure described in Example 16 to afford the title compound: 1H-NMR 400 MHz (CDCl3): δ 6.38 (d, J=8 Hz, 2H), 7.17-7.21 (m, 4H), 7.25-7.31 (m, 4H), 7.42 (d, J=2 Hz, 1H), 8.53 (d, J=8 Hz, 2H), 8.75 (d, J=5 Hz, 2H).

Sources & evidence

ORD record
ord-a0e3b64b62084671afcb6b0043ed07f4
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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