Hydrochloric Acid → HCID 178524065, compound

HRID 270926Notes

Reaction equation

HRID 270926 reaction equation
C([O:3][C:4]([C:6]1[CH:21]=[C:9]2[NH:10][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:12][C:13](=[O:14])[N:8]2[N:7]=1)=[O:5])C.[OH-].[K+].Cl>C(O)C.O1CCOCC1.C(OCC)(=O)C>[O:14]=[C:13]1[N:8]2[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:21]=[C:9]2[NH:10][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178468555HCID 178468555, compound

Product 1

HCID 178524065HCID 178524065, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 50 mg (0.18 mmol) of 7-oxo-5-phenyl-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid ethyl ester in 4 mL of ethanol (EtOH) was added 26 mg (0.40 mmol) of potassium hydroxide (KOH) and the resulting mixture was heated at reflux for 60 h. The reaction mixture was then acidified with 4 M HCl in dioxane solution, and diluted with ethyl acetate. The organic extract was washed with water and brine, dried over sodium sulfate, and concentrated to give desired 7-oxo-5-phenyl-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid as indicated by 1H NMR; LC-MS—calcd for C13H9N3O3 [M++H]+: 256.06, found: 256.1. This corresponds to entry 619.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 60 h
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe5e6fa1294f49b49ff9889fd6089407
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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