Potassium Carbonate → HCID 22030715, compound

HRID 1791683Notes

Reaction equation

HRID 1791683 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1.[OH-].[Na+]>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 178515546HCID 178515546, compound

Product 1

HCID 22030715HCID 22030715, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225 mg, 0.67 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (106 mg, 0.77 mmol) and 2-hydroxyquinoline (111 mg, 0.76 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temperature. The reaction mixture was treated with 1.0 N aqueous sodium hydroxide solution (40 ml) and allowed to stir at ambient temperature for a few minutes. The reaction mixture was extracted 3 times with ethyl acetate and the extracts washed with water and brine. The organic extracts were dried over magnesium sulphate, filtered and the solvent removed by evaporation. The residue was purified by silica column chromatography eluting with dichloromethane/methanol (95/5) to give a solid which was triturated with ether, filtered and dried to give 6-methoxy-7-(3-morpholinopropoxy)-4-(quinolin-2-yloxy)-quinazoiine (33 mg, 11%).

Workup

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. stirringto stir at ambient temperature for a few minutes
  4. extractionThe reaction mixture was extracted 3 times with ethyl acetate
  5. washthe extracts washed with water and brine
  6. dry with materialThe organic extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed by evaporation
  9. customThe residue was purified by silica column chromatography
  10. washeluting with dichloromethane/methanol (95/5)
  11. customto give a solid which
  12. customwas triturated with ether
  13. filtrationfiltered
  14. customdried

Sources & evidence

ORD record
ord-5d09da4ac3df44b0980281c44d3d8b4a
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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