Imidazole → 1-(2-(tert-butyldiphenylsilyloxy)ethyl)-1H-pyrazol-5-amine

HRID 1426976Notes

Reaction equation

HRID 1426976 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:15]([Si:19](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[Si:19]([O:9][CH2:8][CH2:7][N:6]1[C:2]([NH2:1])=[CH:3][CH:4]=[N:5]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 3202812-(5-amino-1H-pyrazol-1-yl)ethan-1-ol

Product 1

HCID 674711071-(2-(tert-butyldiphenylsilyloxy)ethyl)-1H-pyrazol-5-amineYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-(5-amino-1H-pyrazol-1-yl)ethanol (2.07 g, 16.0 mmol) and 1H-imidazole (5.43 g, 79.8 mmol) in DMF (10 mL) was added dropwise tert-butylchlorodiphenylsilane (4.96 mL, 19.1 mmol). The reaction was stirred for 15 hours. The solvent was removed under reduced pressure and the residue was diluted with DCM (40 mL). The organic layer was washed with 1N HCl (10 mL), water (10 mL) and brine (10 mL), then concentrated to give crude desired product (5.62 g, 96.4% yield), which was used in the next step without purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with DCM (40 mL)
  3. washThe organic layer was washed with 1N HCl (10 mL), water (10 mL) and brine (10 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6938a9dcdf894e35bf17fef20caf5ae3
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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