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

HRID 573313Notes

Reaction equation

HRID 573313 reaction equation
[CH2:1]([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)[NH:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](I)[CH3:25].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][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:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1784203873-[4-(Benzyloxy)phenyl]-1H-pyrazolo[3,4-b]pyrazine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-[4-(benzyloxy)phenyl]-1H-pyrazolo[3,4-b]pyrazine (0.58 g), EtI (0.18 ml), and K2CO3 (0.39 g) in DMF (5 mL) was stirred for 3 h at room temperature. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (0.61 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe extract was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-f70957c15b0d4662892c2f4ea56558b1
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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