Water → HCID 67009606, compound

HRID 519805Notes

Reaction equation

HRID 519805 reaction equation
[CH2:1]([N:8]1[C:12]([NH2:13])=[C:11]([CH3:14])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.C([BH3-])#N.[Na+].O>C(O)(=O)C>[CH2:1]([N:8]1[C:12]([NH:13][CH:18]2[CH2:19][CH2:20][O:15][CH2:16][CH2:17]2)=[C:11]([CH3:14])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 121599Tetrahydro-4H-pyran-4-oneHCID 6490672-Benzyl-4-methyl-2H-pyrazol-3-ylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67009606HCID 67009606, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution (50 mL) of 1-benzyl-4-methyl-1H-pyrazol-5-amine (5 g) and tetrahydro-4H-pyran-4-one (3.2 g) in acetic acid was added sodium cyanoborohydride (6.8 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The obtained extract was dried over anhydrous sodium 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 colorless solid (1.9 g, 38%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe obtained residue was poured into saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe obtained extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-80496950513b43978b24a0186afd0453
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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