Triethylamine → 1,3-Di-tert-butyl-1H-pyrazol-5-amine

HRID 1644646Notes

Reaction equation

HRID 1644646 reaction equation
[C:1]([CH2:7][C:8]#[N:9])(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.Cl.[C:18]([NH:22][NH2:23])([CH3:21])([CH3:20])[CH3:19]>C(O)C>[C:18]([N:22]1[C:8]([NH2:9])=[CH:7][C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])=[N:23]1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 433814531,3-Di-tert-butyl-1H-pyrazol-5-amineYield 31.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of pivaloylacetonitrile (300 mg, 2 mmol, 1.0 equiv), triethylamine (1.16 mL, 8.3 mmol, 3.2 equiv), and tert-butylhydrazine hydrochloride (1.03 g, 8.3 mmol, 3.2 equiv) in 10 mL of ethanol was heated at 100° C. in a sealed tube. After 4 days, the reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified via automated flash chromatography (40 g SiO2, ethyl acetate to 20% methanol in ethyl acetate) to afford the product as an off-white solid (123 mg, 20%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified

Sources & evidence

ORD record
ord-bba8f6c91bad49c59229c17493b8534f
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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