Potassium Hydroxide → HCID 68668178, compound

HRID 1188094Notes

Reaction equation

HRID 1188094 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[N:5]=[C:4]([NH:13]C(=O)C)[CH:3]=1.[OH-].[K+].[CH3:19][CH2:20]O.O>>[C:20]1([CH3:19])[CH:4]=[CH:3][CH:2]=[CH:1][C:1]=1[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[N:5]=[C:4]([NH2:13])[CH:3]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 19096565Water ethanolHCID 68666867HCID 68666867, compound

Product 1

HCID 68668178HCID 68668178, compound

Procedure

Crude N-(5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)acetamide (28.86 mmol) was dissolved in EtOH/H2O (2:3, 100 mL) together with potassium hydroxide (11 g, 202 mmol) and was refluxed for 16 hrs. The reaction mixture was concentrated and then extracted with CHCl3. The combined organic layers were washed with brine and dried over Na2SO4. Solvent evaporation and purification by silica gel column chromatography (PE-EtOAc, 7:3 to 3:7) gave 5-tolyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-amine (2.99 g regioisomer A and 4.39 g regioisomer B, 99% over 4 steps).

Workup

  1. temperaturewas refluxed for 16 hrs
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with CHCl3
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customSolvent evaporation and purification by silica gel column chromatography (PE-EtOAc, 7:3 to 3:7)

Sources & evidence

ORD record
ord-de795f4d884a42849c28ec431ae5a38e
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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