Imidazole → 5-(Tert-butyldimethylsilanyloxymethyl)-pyridine-2-carbonitrile

HRID 76354Notes

Reaction equation

HRID 76354 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1.[C:11]([Si:15]([CH3:18])([CH3:17])Cl)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1.O>CN(C)C=O>[Si:15]([O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 122519662-Cyano-5-hydroxymethylpyridine

Product 1

HCID 542127655-(Tert-butyldimethylsilanyloxymethyl)-pyridine-2-carbonitrileYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Hydroxymethyl)pyridine-2-carbonitrile (258 mg) was dissolved in dimethylformamide (8 ml), tert-butyl dimethylchlorosilane (347 mg) and imidazole (326 mg) were added, and the mixture was stirred at room temperature for 1% hr. Water (20 ml) was added and the mixture was stirred, extracted with ethyl acetate (once with 50 ml and once with 20 ml), washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate) to give the title compound (405 mg).

Workup

  1. stirringthe mixture was stirred
  2. extractionextracted with ethyl acetate (once with 50 ml
  3. washonce with 20 ml), washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fa370009765446999623399fc31b82e4
Source dataset
uspto-grants-2014_09
Patent number
US08835631B2

Reaction notes

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