Imidazole → 5-tert-Butyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2H-pyrazol-3-ylamine

HRID 1446653Notes

Reaction equation

HRID 1446653 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1.C(OCC)(=O)C>CN(C=O)C.O>[C:10]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([CH2:7][CH2:8][O:9][Si:18]([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19])[N:5]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 162278772-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)ethan-1-ol

Product 1

HCID 685465445-tert-Butyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2H-pyrazol-3-ylamineYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 2-(5-amino-3-tert-butyl-pyrazol-1-yl)-ethanol (3.42 g, 0.019 mol), add TBDMSCl (3.38 g, 1.2 equiv.) and imidazole (3.18 g, 2.5 equiv.) in DMF (7 mL) and stir overnight at room temperature under N2. Dilute the reaction with ethyl acetate and water. Wash the organic layer with water then saturated aqueous saturated sodium chloride and then dry over magnesium sulfate, filter, and concentrate in vacuo to give a solid (5.5 g, 99%) which is used without further purification. MS (ES), m/z 298 (M+1).

Workup

  1. additionDilute
  2. washWash the organic layer with water
  3. dry with materialsaturated aqueous saturated sodium chloride and then dry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e8707c278882408c8510530b8dd68d62
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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