Imidazole → 3-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-1-phenyl-1H-pyrazol-5-amine

HRID 599321Notes

Reaction equation

HRID 599321 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[CH:3]=1.N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C=O)C>[Si:27]([O:15][CH2:14][C:13]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=1)([CH3:17])[CH3:16])([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 670631642-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropan-1-ol

Product 1

HCID 670630553-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-1-phenyl-1H-pyrazol-5-amineYield 42.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of above 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropan-1-ol (0.208 g, 0.85 mmol) in DMF (2.0 mL) was added imidazole (0.32 g, 4.7 mmol) and TBSCl (0.39 g, 2.6 mmol). The resulting mixture was stirred at RT for 5 h. Solvent was removed under reduced pressure. The residue was diluted with H2O (10 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by chromatography to afford 3-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-1-phenyl-1H-pyrazol-5-amine (0.125 g, 42% yield) as a light yellow oil. MS (ESI) m/z: 346.3 (M+H+).

Workup

  1. customSolvent was removed under reduced pressure
  2. additionThe residue was diluted with H2O (10 mL)
  3. extractionextracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-ac9d1adb257e40d59d418ea6c07bb22e
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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