1-Hexanol → 5-(Hexyloxy)-1-phenyl-1H-pyrazolo[3,4-b]pyrazine

HRID 1462601Notes

Reaction equation

HRID 1462601 reaction equation
[Na].C1(C)C=CC(S([C:11]2[N:12]=[C:13]3[CH:19]=[N:18][N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:14]3=[N:15][CH:16]=2)(=O)=O)=CC=1.[CH2:27]([OH:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>>[CH2:27]([O:33][C:11]1[N:12]=[C:13]2[CH:19]=[N:18][N:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:14]2=[N:15][CH:16]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 3

HCID 81031-HexanolHCID 5360545SodiumHCID 133921465-(4-Methylbenzene-1-sulfonyl)-1-phenyl-1H-pyrazolo[3,4-b]pyrazine

Product 1

HCID 133452895-(Hexyloxy)-1-phenyl-1H-pyrazolo[3,4-b]pyrazineYield 90%

Procedure

In 50 ml of hexanol was dissolved 2.1 g (0.091 mole) of metallic sodium, and then, 14.6 g (0.043 mole) of 5-(4-tolylsulfonyl)-1-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 exessive amount of hexanol was removed by distillation under a reduced pressure. The residue was washed with water, dried and then recrystallized from a benzene/methanol (1:2) mixed solvent to obtain 11.5 g (the yield was 90%) of 5-hexyloxy-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 exessive amount of hexanol was removed by distillation under a reduced pressure
  5. washThe residue was washed with water
  6. customdried
  7. customrecrystallized from a benzene/methanol (1:2)
  8. additionmixed solvent

Sources & evidence

ORD record
ord-0926791b7f2d44acb7073a04346712b0
Source dataset
uspto-grants-1984_07
Patent number
US04460773

Reaction notes

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