Sodium Acetate → Ethyl pyrazolo[1,5-a]pyrimidine-5-carboxylate

HRID 1443839Notes

Reaction equation

HRID 1443839 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10](Cl)[N:9]2[N:13]=[CH:14][CH:15]=[C:8]2[N:7]=1)=[O:5])[CH3:2].C([O-])(=O)C.[Na+]>[Pd].C(OCC)(=O)C.C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]2[N:13]=[CH:14][CH:15]=[C:8]2[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 12366074Ethyl 7-chloropyrazolo[1,5-a]pyrimidine-5-carboxylate

Product 1

HCID 49763022Ethyl pyrazolo[1,5-a]pyrimidine-5-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A suspension of 7-chloro-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid ethyl ester (15.0 g), sodium acetate (6.54 g), and 10% palladium on carbon (665 mg) in ethyl acetate-ethanol (1-1.50 mL) was stirred under a hydrogen atmosphere. After the completion of the reaction, the reactant was filtered, and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with water, aqueous baking soda, and brine, dried with sodium sulfate, and concentrated in vacuo. The yellow residue was recrystallized to yield a light yellow needle crystal (9.9 g, 78%). mp:114-115° C.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reactant was filtered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water, aqueous baking soda, and brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe yellow residue was recrystallized

Sources & evidence

ORD record
ord-0092383681d845dcba430ac49717792e
Source dataset
uspto-grants-2010_02
Patent number
US07662826B2

Reaction notes

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