3-[4-(Benzyloxy)phenyl]-1-ethyl-1H-pyrazolo[3,4-b]pyrazine → 4-(1-Ethyl-1H-pyrazolo[3,4-b]pyrazin-3-yl)phenol

HRID 573314Notes

Reaction equation

HRID 573314 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][N:22]=3)[N:17]([CH2:24][CH3:25])[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.CCOC(C)=O.[Pd]>[CH2:24]([N:17]1[C:18]2=[N:19][CH:20]=[CH:21][N:22]=[C:23]2[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[N:16]1)[CH3:25]

Participants

5

Reactant 1

HCID 866889763-[4-(Benzyloxy)phenyl]-1-ethyl-1H-pyrazolo[3,4-b]pyrazine

Product 1

HCID 1363976954-(1-Ethyl-1H-pyrazolo[3,4-b]pyrazin-3-yl)phenolYield 57.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[4-(benzyloxy)phenyl]-1-ethyl-1H-pyrazolo[3,4-b]pyrazine (570 mg) and 10% Pd—C (50% wet, 200 mg) in MeOH (8 mL) and AcOEt (8 mL) was hydrogenated under balloon pressure at room temperature for 2 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (240 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-2a6fbecf96fb41a28498a42a2c68ae45
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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