2-(4-Iodophenoxy)-4,6-dimethylpyrimidine → (E)-2-(2,6-dichlorobenzamido)-5-[4-(4,6-dimethylpyrimidin-2-yloxy)phenyl]pent-4-enoic acid methyl ester

HRID 1365679

Reaction equation

HRID 1365679 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([NH:8][C:9](=[O:18])[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:17])[CH2:5][CH:6]=[CH2:7].I[C:21]1[CH:35]=[CH:34][C:24]([O:25][C:26]2[N:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[N:27]=2)=[CH:23][CH:22]=1>>[CH3:1][O:2][C:3](=[O:19])[CH:4]([NH:8][C:9](=[O:18])[C:10]1[C:11]([Cl:17])=[CH:12][CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5]/[CH:6]=[CH:7]/[C:21]1[CH:22]=[CH:23][C:24]([O:25][C:26]2[N:27]=[C:28]([CH3:33])[CH:29]=[C:30]([CH3:32])[N:31]=2)=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 577624972-(4-Iodophenoxy)-4,6-dimethylpyrimidineHCID 577625182-(2,6-Dichlorobenzamido)pent-4-enoic acid methyl ester

Product 1

HCID 57762504(E)-2-(2,6-dichlorobenzamido)-5-[4-(4,6-dimethylpyrimidin-2-yloxy)phenyl]pent-4-enoic acid methyl esterYield 56.5%

Procedure

In the same manner as in Example 1, 2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester (47 mg) was reacted with 2-(4-iodophenoxy)-4,6-dimethylpyrimidine (56 mg) to obtain (E)-2-(2,6-dichlorobenzamido)-5-[4-(4,6-dimethylpyrimidin-2-yloxy)phenyl]pent-4-enoic acid methyl ester (44 mg). Column chromatography (silica gel, eluent: hexane/ethyl acetate=2/1) was used for purification.

Sources & evidence

ORD record
ord-a0be25372bd642f69d49c434b82c119d
Source dataset
uspto-grants-2011_02
Patent number
US07893046B2

Linked notes

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