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

HRID 911090Notes

Reaction equation

HRID 911090 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 room temperature for 2 hours. 2-chloro-4-nitropyridine (15 g, 95 mmol) was then added and the reaction stirred overnight at room temperature. The material was diluted with water and extracted with ethylacetate. The organic layer was dried, and concentrated. Flash chromatography (dichloromethane/methanol 20:1) gave (5-(2-chloropyridin-4-yloxy)-4,6-dimethylpyridin-3-yl)methanol (19.8 g, 79%) as colorless oil.

Workup

  1. stirringthe reaction stirred overnight at room temperature
  2. extractionextracted with ethylacetate
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b4adcbeebfe74e1bb20d96d0d4c3535b
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…