1-Bromo-2-Chloroethane → 4-Chloro-7-(2-chloroethoxy)-6-methoxyquinazoline

HRID 1785155Notes

Reaction equation

HRID 1785155 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.Br[CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:16][CH2:17][Cl:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

Product 1

HCID 596829074-Chloro-7-(2-chloroethoxy)-6-methoxyquinazolineYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-chloro-6-methoxyquinazolin-7-ol (1.2 g, 5.8 mmol), 1 bromo 2 chloroethane (5.69 ml, 6.8 mmol), potassium carbonate (2.36 g, 17.4 mmol) and dimethylformamide (15 ml) were heated to 90 C for 1.5 hours. The excess potassium carbonate was filtered off and the reaction evaporated under reduced pressure. The residue was purified by flash chromatography on silica eluting with a mixture of 60-100% dichlormethane in hexane and 30-50% ethyl acetate in hexane to give 4-chloro-7-(2-chloroethoxy)-6-methoxyquinazoline as a solid (0.89 g, 57%). NMR Spectrum: (CDCl3) 3.98 (t, 2H), 4.08 (s, 3H), 4.47 (t, 2H), 7.36 (s, 1H), 7.42 (s, 1H), 8.87 (s, 1H). Mass Spectrum: M+H+ 273.

Workup

  1. temperaturewere heated to 90 C for 1.5 hours
  2. filtrationThe excess potassium carbonate was filtered off
  3. customthe reaction evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica eluting with a mixture of 60-100% dichlormethane in hexane and 30-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7e87489c86c8491dbb4136f96c54b9cd
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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