Sodium hydride → (5-(2-Chloropyridin-4-yloxy)-4,6-dimethylpyridin-3-yl)methanol

HRID 1972154Notes

Reaction equation

HRID 1972154 reaction equation
[H-].[Na+].Cl.[OH:4][CH2:5][C:6]1[C:7]([CH3:14])=[C:8]([OH:13])[C:9]([CH3:12])=[N:10][CH:11]=1.[Cl:15][C:16]1[CH:21]=[C:20]([N+]([O-])=O)[CH:19]=[CH:18][N:17]=1>CN(C=O)C.O>[Cl:15][C:16]1[CH:21]=[C:20]([O:13][C:8]2[C:7]([CH3:14])=[C:6]([CH2:5][OH:4])[CH:11]=[N:10][C:9]=2[CH3:12])[CH:19]=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 674174-Desoxypyridoxine hydrochlorideHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 86634791(5-(2-Chloropyridin-4-yloxy)-4,6-dimethylpyridin-3-yl)methanolYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of sodium hydride (5.27 g, 209 mmol) in DMF (100 mL) was carefully charged with 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride (18 g, 95 mmol). The mixture stirred at ambient temperature for 2 hours. 2-chloro-4-nitropyridine (15 g, 95 mmol) was then added and the reaction stirred overnight at ambient temperature. The material was diluted with water and extracted with ethyl acetate. The organic layer was dried, and concentrated. Flash chromatography (dichloromethane/methanol 20:1) gave the title compound (19.8 g, 79%) as colorless oil.

Workup

  1. stirringthe reaction stirred overnight at ambient temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-53a3bb9de52b4f7e895ff90dd287a19c
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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