Formamidine acetate → HCID 22648741, compound

HRID 393157Notes

Reaction equation

HRID 393157 reaction equation
C[O-].[Na+].C(O)(=O)C.[CH:8]([NH2:10])=[NH:9].C(O[CH:14]=[C:15]([C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[C:16](=O)[C:17]([F:20])([F:19])[F:18])C>CO>[CH:23]([C:22]([C:15]1[C:16]([C:17]([F:18])([F:19])[F:20])=[N:9][CH:8]=[N:10][CH:14]=1)=[O:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 86759544HCID 86759544, compound

Product 1

HCID 22648741HCID 22648741, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

46 g (0.85 mol) of sodium methoxide was dissolved in 700 ml of methanol, and 76 g (0.73 mol) of formamidine acetate was added, followed by stirring at room temperature for 15 minutes. Then, 146 g (0.61 mol) of 3-ethoxymethylene-1,1,1-trifluoro-5-methyl-2,4-hexanedione was added under cooling with ice, followed by heating and refluxing for further 2 hours. The solvent was distilled off under reduced pressure, and 1,000 ml of ice water was added, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate=6:1) to obtain 89 g (yield: 67%) of 5-isopropylcarbonyl-4-trifluoromethylpyrimidine as slightly yellow liquid.

Workup

  1. temperatureunder cooling with ice
  2. temperatureby heating
  3. temperaturerefluxing for further 2 hours
  4. distillationThe solvent was distilled off under reduced pressure, and 1,000 ml of ice water
  5. additionwas added
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe obtained organic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationEthyl acetate was distilled off under reduced pressure
  10. customthe obtained crude product
  11. customwas purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-ce008569be8b4545848b2546ef24fe5a
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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