2,4-Dimethylphenol → [5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid 2,4-dimethyl-phenyl ester

HRID 348456Notes

Reaction equation

HRID 348456 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[CH3:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1O>CO.ClCCl>[CH3:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[O:20][C:19](=[O:21])[CH2:18][O:17][C:14]1[N:13]=[CH:12][C:11]([C:9](=[O:10])[NH:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 77712,4-DimethylphenolHCID 21087356[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid

Product 1

HCID 69522908[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid 2,4-dimethyl-phenyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The titled compound was prepared from [5-(4-fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid using 2,4-dimethylphenol (16 mg, 0.13 mmol) as the source alcohol. Chromatography (5% methanol/dichloromethane) through SiO2 yielded 48 mg (71%) of the titled compound as a white solid. ESI-MS m/z 396 (MH+), 394 (M−H−).

Sources & evidence

ORD record
ord-82eea71ddb4648a9affc0a63cbf12e45
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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