Imidazole → 5-tert-Butyl-2-(3-triisopropylsilanyloxy-phenyl)-2H-pyrazol-3-ylamine

HRID 75602Notes

Reaction equation

HRID 75602 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[NH2:12][C:13]1[N:17]([C:18]2[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=2)[N:16]=[C:15]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:14]=1.N1C=CN=C1>CN(C=O)C>[C:25]([C:15]1[CH:14]=[C:13]([NH2:12])[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])[CH:19]=2)[N:16]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 595579663-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenol

Product 1

HCID 866867005-tert-Butyl-2-(3-triisopropylsilanyloxy-phenyl)-2H-pyrazol-3-ylamineYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triisopropylsilylchloride (1.02 mL, 3.96 mmol) was added to a solution of 3-(5-amino-3-tert-butyl-pyrazol-1-yl)-phenol (915 mg, 3.96 mmol) and imidazole (646 mg, 9.50 mmol) in DMF (15 mL) at 0° C. The reaction was stirred at RT over the weekend then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-40% EtOAc in cyclohexane, to give the title compound (1.53 g, 99%). LCMS (Method 4): Rt 4.78 min, m/z 388 [MH+].

Workup

  1. customthen partitioned between EtOAc and water
  2. extractionThe aqueous layer was then extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-2f5bd3442d214e6f991724730827f825
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Reaction notes

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