4-Amino-2,6-dichloropyridine → 2-Chloro-6-methoxypyridin-4-amine

HRID 1628278Notes

Reaction equation

HRID 1628278 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH3:10][O-:11].[Na+].CO>O>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([O:11][CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 1376524-Amino-2,6-dichloropyridineHCID 23694274Sodium methanolate methanol

Product 1

HCID 713025122-Chloro-6-methoxypyridin-4-amineYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,6-dichloropyridin-4-amine 41.6.A (available from Aldrich) (3.10 g, 19.0 mmol) in 20% NaOMe/MeOH (15 mL) was refluxed for 72 hr. The reaction mixture was diluted with H2O (40 mL) and extracted with 30% iPrOH/CHCl3 (3×30 mL). The combined organic layers were washed with water (2×20 mL), brine (15 mL) and dried over MgSO4. After removal of organic solvents under reduced pressure, purification of the residue by flash chromatography on silica gel using 0-10% MeOH/CH2Cl2 for elution gave title product 41.6.B as white solid (2.45 g, 81.2%).

Workup

  1. extractionextracted with 30% iPrOH/CHCl3 (3×30 mL)
  2. washThe combined organic layers were washed with water (2×20 mL), brine (15 mL)
  3. dry with materialdried over MgSO4
  4. customAfter removal of organic solvents
  5. customunder reduced pressure, purification of the residue by flash chromatography on silica gel using 0-10% MeOH/CH2Cl2
  6. washfor elution

Sources & evidence

ORD record
ord-69d0d4fcd0004fba9bfd414429d8790c
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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