Water → HCID 49761527, compound

HRID 1393657Notes

Reaction equation

HRID 1393657 reaction equation
[OH:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:17])[C:3]=1[C:18]([O:20]CC)=[O:19].[C:23](=O)([O-])[O-].[K+].[K+].CI.O>CC(C)=O>[CH3:23][O:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:17])[C:3]=1[C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469172HCID 178469172, compound

Product 1

HCID 49761527HCID 49761527, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The ethyl 7-hydroxy-5-methyl-2-phenylpyrazolo[1.5-a]pyrimidine-6-carboxylate (297 mg) obtained above was suspended in acetone (5 ml), and potassium carbonate (138 mg) was added thereto and stirred for 30 minutes at room temperature. Methyl iodide (1.0 ml) was added to the mixture which was then refluxed for 2 hours. The reaction mixture was cooled to room temperature, and water was added to the reaction mixture which was extracted with chloroform, and the organic phase was washed with a saturated saline solution and dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure, and the resulting crystals were dissolved in ethanol (5 ml). 5 N Sodium hydroxide solution (1 ml) was added thereto and stirred for 1 hour at 50° C. The reaction mixture was cooled to room temperature, and water was added to the mixture which was then washed with ethyl acetate. 2 N Hydrochloric acid was added to the aqueous phase until it became acidic, and precipitated crystals were collected by filtration and washed with water and n-hexane. The crystals were dried under reduced pressure to give the title compound (121 mg, Y.:45%) as white crystals.

Workup

  1. temperaturewas then refluxed for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionwas extracted with chloroform
  4. washthe organic phase was washed with a saturated saline solution
  5. dry with materialdried over sodium sulfate anhydrous
  6. concentrationThe product was concentrated under reduced pressure
  7. dissolutionthe resulting crystals were dissolved in ethanol (5 ml)
  8. addition5 N Sodium hydroxide solution (1 ml) was added
  9. stirringstirred for 1 hour at 50° C
  10. temperatureThe reaction mixture was cooled to room temperature
  11. additionwater was added to the mixture which
  12. washwas then washed with ethyl acetate
  13. addition2 N Hydrochloric acid was added to the aqueous phase until it
  14. customprecipitated crystals
  15. filtrationwere collected by filtration
  16. washwashed with water and n-hexane
  17. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-158cf4cae44b409988b5d944efab2386
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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