Phenol → HCID 178437892, compound

HRID 2257055Notes

Reaction equation

HRID 2257055 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12](S(C)(=O)=O)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:20][CH3:21])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+]>O>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([O:28][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:20][CH3:21])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 178437894HCID 178437894, compound

Product 1

HCID 178437892HCID 178437892, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-6-(methylsulfonyl)pyrazolo[3,4-d]pyrimidin-4-one (3 g, 9.6 mmol), phenol (6 g, 64 mmol) and NaH (0.5 g, 12.8 mmol, 60% dispersion in mineral oil) was heated at 170°-175° C. for 5 hours. The reaction mixture was poured into water (50 mL) and extracted with CHCl3 (100 mL). The CHCl3 layer was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with 10% ether/hexane to afford 2.1 g (68%) of 1-cyclopentyl-3-ethyl-6-(phenyloxy)pyrazolo[3,4-d]pyrimidin-4-one, as a white solid, m.p. 175°-177° C.

Workup

  1. temperaturewas heated at 170°-175° C. for 5 hours
  2. extractionextracted with CHCl3 (100 mL)
  3. concentrationThe CHCl3 layer was concentrated in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with 10% ether/hexane

Sources & evidence

ORD record
ord-05bda5a470994e628d9dbb6d9854c030
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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