Potassium Carbonate → 6-Methoxy-4-(4-methylquinolin-7-yloxy)-7-(3-morpholinopropoxy)quinazoline

HRID 453989Notes

Reaction equation

HRID 453989 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]=[C:39]2[C:34]([C:35]([CH3:41])=[CH:36][CH:37]=[N:38]2)=[CH:33][CH: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]=[C:39]2[C:34]([C:35]([CH3:41])=[CH:36][CH:37]=[N:38]2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 1354918544-Methyl-7-quinolinol

Product 1

HCID 220306816-Methoxy-4-(4-methylquinolin-7-yloxy)-7-(3-morpholinopropoxy)quinazolineYield 57%

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 7-hydroxy-4-methylquinoline (122 mg, 0.77 mmol), (Chem. Berich. 1967, 100, 2077), in DMF (7.5 ml) was stirred at 100° C. for 5 hours then allowed to cool to ambient temperature. The reaction mixture was treated with 1M aqueous sodium hydroxide solution (40 ml) and stirred at ambient temperature for a few minutes. The crude solid was collected by filtration washing with water. The resultant solid was dissolved in dichloromethane (2 ml) and was filtered through phase separating paper. The filtrate was evaporated under vacuum to give a solid residue which was triturated with ether, filtered and dried to give 6-methoxy-4-(4-methylquinolin-7-yloxy)-7-(3-morpholinopropoxy)quinazoline (175 mg, 57%).

Workup

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. stirringstirred at ambient temperature for a few minutes
  4. filtrationThe crude solid was collected by filtration
  5. washwashing with water
  6. dissolutionThe resultant solid was dissolved in dichloromethane (2 ml)
  7. filtrationwas filtered through phase
  8. customseparating paper
  9. customThe filtrate was evaporated under vacuum
  10. customto give a solid residue which
  11. customwas triturated with ether
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-cd37c94797654ad9a054131b410706dc
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

Loading…