Diisopropylethylamine → HCID 58980642, compound

HRID 735785Notes

Reaction equation

HRID 735785 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:10]([OH:13])=[CH:11][N:12]=1)[C:8]#[N:9])([CH3:4])([CH3:3])[CH3:2].[CH:14](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C>C(#N)C.CO>[C:1]([C:5]1[CH:6]=[C:7]([C:10]([O:13][CH3:14])=[CH:11][N:12]=1)[C:8]#[N:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 126342602-(1,1-Dimethylethyl)-5-hydroxy-4-pyridinecarbonitrile

Product 1

HCID 58980642HCID 58980642, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

To a solution of 2-tert-butyl-5-hydroxy-isonicotinonitrile (10.0 g, 73.5 mmol) in acetonitrile/methanol (9:1, 20 mL) was added N,N-diisopropylethylamine (1.48 mL, 8.52 mmol) followed by (trimethylsilyl)diazomethane (2.0M in hexane, 4.30 mL, 8.52 mmol). The red solution was stirred for 18 h at room temperature and then concentrated in vacuo. The residue was dissolved in methylene chloride, washed with saturated aqueous NaHCO3 dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-tert-butyl-5-methoxy-isonicotinonitrile (1.10 g, 99%) as a pale yellow oil which was utilized without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a748733d8c2448cbad4a6029661f29b
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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