Ethyl 4,4,4-trifluoroacetoacetate → HCID 178516161, compound

HRID 1289852Notes

Reaction equation

HRID 1289852 reaction equation
[NH:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].[F:9][C:10]([F:20])([F:19])[C:11](=O)[CH2:12][C:13](OCC)=[O:14]>C(O)(=O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[N:8][C:3]=1[N:1]1[C:13]([OH:14])=[CH:12][C:11]([C:10]([F:20])([F:19])[F:9])=[N:2]1

Participants

4

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 3465582-Hydrazinylpyrimidine

Product 1

HCID 178516161HCID 178516161, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2 g (9 mmol) of 2-hydrazinopyrimidine and ethyl trifluoroacetoacetate (2.6 ml; 9.1 mmol) in 10 ml of acetic acid was refluxed for 60 hours with stirring under nitrogen and then cooled. The mixture was concentrated in vacuo, the residue was diluted with 100 ml of water, and the mixture was extracted with ethyl acetate (3×). The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was dried in vacuo to afford 700 mg of 1-(2-pyrimidinyl)-3-trifluoromethyl-5-hydroxypyrazole as a red gum.

Workup

  1. temperaturewas refluxed for 60 hours
  2. temperaturecooled
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe residue was diluted with 100 ml of water
  5. extractionthe mixture was extracted with ethyl acetate (3×)
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was dried in vacuo

Sources & evidence

ORD record
ord-db3e432a97484938bebc608c06dce22e
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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