Diisopropylethylamine → HCID 58980642, compound

HRID 1787455Notes

Reaction equation

HRID 1787455 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].[CH3:14]CN(C(C)C)C(C)C.C[Si](C=[N+]=[N-])(C)C>CC#N.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 10.0 g (73.5 mmol) of 2-tert-Butyl-5-hydroxy-isonicotinonitrile ((a) J. Med. Chem. 1981, 24, 115 (b) U.S. Pat. No. 4,123,537) in MeCN/MeOH (9:1, 20 mL) was added iPr2NEt (1.48 mL, 8.52 mmol) followed by (trimethylsilyl)diazomethane (2.0 M in hexane, 4.30 mL, 8.52 mmol). The red solution was stirred 18 h at rt then concentrated. The residue was dissolved in CH2Cl2, washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated 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. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6610abeb5d346dc835b987355061fa9
Source dataset
uspto-grants-2009_03
Patent number
US07511042B2

Reaction notes

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