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O-Cresol → 2-[2-(5-fluoro-6-o-tolyloxy-pyrimidin-4-yloxy)-phenyl]-2-methoxyimino-N-methyl-acetamide

HRID 278377
Notes
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Reaction equation

HRID 278377 reaction equation
[H-].[Na+].[F:3][C:4]1[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18](=[N:23][O:24][CH3:25])[C:19]([NH:21][CH3:22])=[O:20])=[N:6][CH:7]=[N:8][C:9]=1F.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33]>CN(C)C=O>[F:3][C:4]1[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18](=[N:23][O:24][CH3:25])[C:19]([NH:21][CH3:22])=[O:20])=[N:6][CH:7]=[N:8][C:9]=1[O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 335O-CresolHCID 24758Sodium hydrideHCID 53688888HCID 53688888, compound

Product 1

HCID 544742242-[2-(5-fluoro-6-o-tolyloxy-pyrimidin-4-yloxy)-phenyl]-2-methoxyimino-N-methyl-acetamideYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

With cooling, 0.25 g (0.0062 mol) of sodium hydride (60%) are added to a mixture of 2 g (0.0062 mol) of 2-[2-(5,6-difluoropyrimidin-4-yloxy)-phenyl]-2-methoxyimino-N-methyl-acetamide and 0.67 g (0.0062 mol) of 2-methylphenol in 20 ml of dimethylformamide, and the mixture is stirred at 25° C. for 12 hours. The reaction mixture is poured onto water and extracted with ethyl acetate, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. 1.5 g (58.9%) of 2-[2-(5-fluoro-6-o-tolyloxy-pyrimidin-4-yloxy)-phenyl]-2-methoxyimino-N-methyl-acetamide are obtained.

Workup

  1. temperatureWith cooling
  2. additionThe reaction mixture is poured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-681c321d0e184ccc80730c38bd91f7c9
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06359133B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes