Ethyl pivaloylacetate → HCID 178503602, compound

HRID 636411Notes

Reaction equation

HRID 636411 reaction equation
[C:1]1([S:7]([C:10]2[C:14]([S:15][CH3:16])=[N:13][NH:12][C:11]=2[NH2:17])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([CH2:24][C:25](OCC)=[O:26])(=O)[C:19]([CH3:22])([CH3:21])[CH3:20]>O>[C:1]1([S:7]([C:10]2[C:14]([S:15][CH3:16])=[N:13][N:12]3[C:25]([OH:26])=[CH:24][C:18]([C:19]([CH3:22])([CH3:21])[CH3:20])=[N:17][C:11]=23)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 86950Ethyl pivaloylacetateHCID 110547174-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamine

Product 1

HCID 178503602HCID 178503602, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g (7.4 mmol) of 4-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamine and 2.91 ml (18.3 mmol) of ethyl pivaloylacetate were added to 27 g of polyphosphoric acid and heated to 120° for 5 hrs. After cooling 100 ml of water were slowly added thereto and the mixture was extracted three times with CH2Cl2. The organic phase was dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/EtOAc) yielded 1.34 g (48%) of 3-benzenesulphonyl-5-tert-butyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol as a colorless foam.

Workup

  1. temperatureheated to 120° for 5 hrs
  2. additionwere slowly added
  3. extractionthe mixture was extracted three times with CH2Cl2
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e2d6403078d34d26b651d9600cc0d643
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

Loading…