Hydrazine hydrate (1:1) → 3-[4-(Benzyloxy)phenyl]-1H-pyrazolo[3,4-b]pyrazine

HRID 573312Notes

Reaction equation

HRID 573312 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:22](Cl)=[N:21][CH:20]=[CH:19][N:18]=2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:25][NH2:26]>CCO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:17]3[C:22](=[N:21][CH:20]=[CH:19][N:18]=3)[NH:26][N:25]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86688975[4-(Benzyloxy)phenyl](3-chloropyrazin-2-yl)methanone

Product 1

HCID 1784203873-[4-(Benzyloxy)phenyl]-1H-pyrazolo[3,4-b]pyrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of [4-(benzyloxy)phenyl](3-chloropyrazin-2-yl)methanone (1.23 g) in EtOH (20 mL) was added hydrazine hydrate (0.37 mL) at room temperature, and the mixture was refluxed for 2 h. The mixture was concentrated under reduced pressure. The residue was partitioned between AcOEt/THF (1/1) and saturated NaHCO3 aqueous solution. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residual crystals were recrystallized from THF/AcOEt to give the title compound (0.60 g).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between AcOEt/THF (1/1) and saturated NaHCO3 aqueous solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residual crystals were recrystallized from THF/AcOEt

Sources & evidence

ORD record
ord-ec31a5af3b694cb7af7fbaa594a3df10
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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