Water → Quinazoline, 2-chloro-4,6-dimethoxy-

HRID 1666654Notes

Reaction equation

HRID 1666654 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH3:15][O-:16].[Na+].O>CO>[Cl:1][C:2]1[N:11]=[C:10]([O:16][CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 99913972,4-Dichloro-6-methoxyquinazolineHCID 10942334Sodium Methoxide

Product 1

HCID 57970127Quinazoline, 2-chloro-4,6-dimethoxy-Yield 61.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,4-dichloro-6-methoxyquinazoline (0.33 g) in methanol (5 mL) was added sodium methoxide (0.086 g), and the mixture was stirred at room temperature for 6 h. Water was added to the reaction mixture, and the aqueous layer was extracted with chloroform. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform/methanol=50:1) to obtain 2-chloro-4,6-dimethoxyquinazoline (0.20 g).

Workup

  1. extractionthe aqueous layer was extracted with chloroform
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (silica gel, chloroform/methanol=50:1)

Sources & evidence

ORD record
ord-6d727b1e7438465ca9d6a98437927d71
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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