1-(1H-Imidazol-1-yl)ethanone → HCID 178437886, compound

HRID 1600806Notes

Reaction equation

HRID 1600806 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([CH2:16]OS(C)(=O)=O)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:22][CH3:23])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CC([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)=O.C([O-])(O)=O.[Na+]>CC#N>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([CH2:16][C:28]4[NH:27][CH:31]=[CH:30][N:29]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:22][CH3:23])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 516892Sodium BicarbonateHCID 178437889HCID 178437889, compound

Product 1

HCID 178437886HCID 178437886, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-6-(methylsulfonyloxy methyl)pyrazolo[3,4-d]pyrimidin-4-one (1.8 g, 15.3 mmol), 1-(methylcarbonyl)imidazole (640 mg, 5.8 mmol) and CH3CN (36 mL) was heated at reflux for 6 hours. The solvent was stripped, ice water and saturated NaHCO3 were added and the mixture was extracted with ethyl acetate, dried over MgSO4, filtered and stripped. The product was combined with that from a similar experimental run and the mixture was recrystallized from ethyl acetate. The product was then treated with 2N HCl, extracted with ethyl acetate and the aqueous layer was neutralized with NaHCO3, extracted with ethyl acetate, dried over MgSO4, filtered and stripped. The residue was recrystallized from ethyl acetate to afford 0.54 g of 1-cyclopentyl-3-ethyl-6-(1-imidazolylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 252-253° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe mixture was recrystallized from ethyl acetate
  7. additionThe product was then treated with 2N HCl
  8. extractionextracted with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e4daab8ec9af4149a25b210aa0edb995
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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