Phenol → HCID 178437892, compound

HRID 1600826Notes

Reaction equation

HRID 1600826 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

Conditions

Temperature
172.5 °C

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. extractionextracted with CHCl3 (100 mL)
  2. concentrationThe CHCl3 layer was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel eluting with 10% ether/hexane

Sources & evidence

ORD record
ord-b6349e3b09b14024a30cd7a8eaa885d7
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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