Potassium Carbonate → HCID 53688888, compound

HRID 432062Notes

Reaction equation

HRID 432062 reaction equation
[CH3:1][NH:2][C:3](=[O:15])[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])=[N:5][O:6][CH3:7].C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]1[C:28]([F:29])=[C:27](F)[N:26]=[CH:25][N:24]=1>C(#N)C>[CH3:1][NH:2][C:3](=[O:15])[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:27]1[C:28]([F:29])=[C:23]([F:22])[N:24]=[CH:25][N:26]=1)=[N:5][O:6][CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 35727644,5,6-TrifluoropyrimidineHCID 136045378N-methyl-2-(2-hydroxyphenyl)-2-methoxyiminoacetamide

Product 1

HCID 53688888HCID 53688888, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

6 g (0.0280 mol) of N-methyl-2-(2-hydroxyphenyl)-2-methoxyiminoacetamide (Example I-1g from process step 1; HPLC: 43.7% N-methyl-E-2-(2-hydroxyphenyl)-2-methoxyimino-acetamide of log p=0.98 and 53.5% N-methyl-Z-2-(2-hydroxyphenyl)-2-methoxyiminoacetamide of log p=1.29) are dissolved in 80 ml of acetonitrile. The solution is cooled to 0° C., 4.7 g (0.034 mol) of potassium carbonate are added and the mixture is stirred for another 30 minutes. 3.8 g (0.0283 mol) of 4,5,6-trifluoropyrimidine are then added dropwise and the mixture is stirred at 20° C. for two hours. The solvent is then distilled off under reduced pressure, the residue is mixed with water, the product is extracted with ethyl acetate, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 5.7 g (61.4% of theory) of crude N-methyl-2-[2-(5,6-difluoropyrimidin-4-yloxy)phenyl]-2-methoxyiminoacetamide which, according to HPLC, contains 45.5% N-methyl-E-2-[2-(5,6-difluoropyrimidin-4-yloxy)-phenyl]-2-methoxyiminoacetamide of log p=1.95 and 46.6% N-methyl-Z-2-[2-(5,6-difluoro-pyrimidin-4-yloxy)phenyl]-2-methoxyiminoacetamide of log p=1.87.

Workup

  1. stirringthe mixture is stirred at 20° C. for two hours
  2. distillationThe solvent is then distilled off under reduced pressure
  3. additionthe residue is mixed with water
  4. extractionthe product is extracted with ethyl acetate
  5. dry with materialthe organic phase is dried over sodium sulphate
  6. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-fc3583a5d8e24ec1a816216ed5edd7f8
Source dataset
uspto-grants-2003_12
Patent number
US06660872B1

Reaction notes

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