Ethyl Acetoacetate → HCID 21255037, compound

HRID 636419Notes

Reaction equation

HRID 636419 reaction equation
[C:1]1([S:7]([C:10]2[C:11]([NH2:15])=[N:12][NH:13][CH:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](OCC)(=O)[CH2:17][C:18]([CH3:20])=O>C(O)(=O)C>[C:1]1([S:7]([C:10]2[CH:14]=[N:13][N:12]3[CH:16]=[CH:17][C:18]([CH3:20])=[N:15][C:11]=23)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 178509275HCID 178509275, compound

Product 1

HCID 21255037HCID 21255037, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.0 g (4.47 mmol) of 4-benzenesulphonyl-1H-pyrazol-3-ylamine and 0.6 ml (5.37 mmol) of ethyl acetoacetate in 8 ml of acetic acid was heated at reflux for 1.5 hrs. The reaction solution was cooled to RT and evaporated. The residue was partitioned between CH2Cl2 and H2O and the aqueous phase was washed three times with 150 ml of CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 20:1) yielded 0.91 g (70%) of 3-benzenesulphonyl-5-methyl-pyrazolo[1,5-a]pyrimidine as beige crystals.

Workup

  1. temperatureat reflux for 1.5 hrs
  2. customevaporated
  3. customThe residue was partitioned between CH2Cl2 and H2O
  4. washthe aqueous phase was washed three times with 150 ml of CH2Cl2
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0554d3f45ebe45fd88e03b2157cf81d7
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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