Imidazole → HCID 178437853, compound

HRID 1736591Notes

Reaction equation

HRID 1736591 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[C:20]([CH3:22])[N:19]=[C:18](Cl)[CH:17]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:24][CH3:25])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1>CN1CCCC1=O>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([N:26]5[CH:30]=[CH:29][N:28]=[CH:27]5)[CH:17]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:24][CH3:25])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 178437852HCID 178437852, compound

Product 1

HCID 178437853HCID 178437853, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-6-(2-chloro-6-methyl-4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-one (0.30 g, 0.84 mmol), imidazole (0.06 g, 0.9 mmol) and N-methyl-2-pyrrolidinone (10 ml) was refluxed for 60 hours. The mixture was cooled to room temperature, filtered through a plug of celite and the plug was rinsed with methanol. The solvent was removed in vacuo and the residue was washed with ethanol and the solution was filtered. The filtrate was treated with charcoal, filtered, and the solvent was removed in vacuo. The residue was triturated with ether and a dark solid was collected by filtration. The product was recrystallized from ether/methanol to afford 0.018 g (10%) of 1-cyclopentyl-3-ethyl-6-[2-(1-imidazolyl)-6-methyl-4-pyridyl]pyrazolo[3,4-d]pyrimidin-4-one. 1/4 hydrate as a beige powder, m.p. 277°-278° C.

Workup

  1. temperaturewas refluxed for 60 hours
  2. filtrationfiltered through a plug of celite
  3. washthe plug was rinsed with methanol
  4. customThe solvent was removed in vacuo
  5. washthe residue was washed with ethanol
  6. filtrationthe solution was filtered
  7. additionThe filtrate was treated with charcoal
  8. filtrationfiltered
  9. customthe solvent was removed in vacuo
  10. customThe residue was triturated with ether
  11. filtrationa dark solid was collected by filtration
  12. customThe product was recrystallized from ether/methanol

Sources & evidence

ORD record
ord-87451e7a2e734ff8b730bd04f9714c2b
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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