(+-)-2-Butanol → 5-[(Butan-2-yl)oxy]-1-phenyl-1H-pyrazolo[3,4-b]pyrazine

HRID 1462600Notes

Reaction equation

HRID 1462600 reaction equation
[Na].Cl[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][N:17]=[C:12]3[CH:11]=[N:10]2)[CH:8]=1.[CH:18]([OH:22])([CH2:20][CH3:21])[CH3:19]>>[CH:18]([O:22][C:16]1[N:17]=[C:12]2[CH:11]=[N:10][N:9]([C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:8]=3)[C:13]2=[N:14][CH:15]=1)([CH2:20][CH3:21])[CH3:19]

Participants

4

Reactant 3

HCID 6568(+-)-2-ButanolHCID 5360545SodiumHCID 20453742HCID 20453742, compound

Product 1

HCID 133452865-[(Butan-2-yl)oxy]-1-phenyl-1H-pyrazolo[3,4-b]pyrazineYield 53%

Procedure

In 50 ml of sec.-butanol was dissolved 2.1 g (0.091 mole) of metallic sodium, and then, 10.0 g (0.043 mole) of 5-chloro-phenyl-1H-pyrazolo[3,4-b]pyrazine was added to the solution. The mixture was heated under reflux for 2 hours. After completion of the reaction, the excessive amount of sec.-butanol was removed by distillation under a reduced pressure. The residue was washed with water, dried and then recrystallized from hexane to obtain 6.2 g (the yield was 53%) of 5-sec.-butoxy-1-phenyl-1H-pyrazolo[3,4-b]pyrazine in the form of a colorless needle crystal.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter completion of the reaction
  4. customthe excessive amount of sec.-butanol was removed by distillation under a reduced pressure
  5. washThe residue was washed with water
  6. customdried
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-d27bd80646484820bab705440854b0d1
Source dataset
uspto-grants-1984_07
Patent number
US04460773

Reaction notes

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