1-Benzyl-1H-pyrazol-5-amine → 1-benzyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine

HRID 1412582Notes

Reaction equation

HRID 1412582 reaction equation
[CH2:1]([N:8]1[C:12]([NH2:13])=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[C:12]([NH:13][CH:17]2[CH2:18][CH2:19][O:14][CH2:15][CH2:16]2)=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 770611-Benzyl-1H-pyrazol-5-amineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 287679511-benzyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amineYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-benzyl-1H-pyrazol-5-amine (2.09 g) in acetic acid (20 mL) was added tetrahydro-4H-pyran-4-one (1.25 g), and the mixture was stirred at room temperature for 30 min. After stirring, sodium triacetoxyborohydride (3.90 g) was added at room temperature, and the mixture was stirred overnight. Acetic acid was evaporated under reduced pressure and ethyl acetate and water were added to the residue. The mixture was neutralized with sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow oil (3.00 g, 97%).

Workup

  1. stirringAfter stirring
  2. stirringthe mixture was stirred overnight
  3. customAcetic acid was evaporated under reduced pressure and ethyl acetate and water
  4. additionwere added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8fd2a82e3de0436a9aee4c5bad205b08
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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