Potassium Carbonate → 6-Methoxy-7-(3-morpholinopropoxy)-4-(quinolin-5-yloxy)-quinazoline

HRID 454159Notes

Reaction equation

HRID 454159 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][CH:38]=[C:37]2[C:32]=1[CH:33]=[CH:34][CH:35]=[N:36]2.[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][CH:38]=[C:37]2[C:32]=1[CH:33]=[CH:34][CH:35]=[N:36]2

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 135441757Quinolin-5-ol

Product 1

HCID 220305986-Methoxy-7-(3-morpholinopropoxy)-4-(quinolin-5-yloxy)-quinazolineYield 59.5%

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 5-hydroxyquinoline (111 mg, 0.77 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 resulting precipitate was filtered off, washed with water and air dried for a short while. The damp solid was dissolved in dichloromethane, filtered through phase separating paper and the filtrate evaporated under vacuum. The residue was triturated with ether, filtered and dried to give 6-methoxy-7-(3-morpholinopropoxy)-4-(quinolin-5-yloxy)-quinazoline (178 mg, 59%).

Workup

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. stirringto stir at ambient temperature for a few minutes
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with water and air
  6. customdried for a short while
  7. dissolutionThe damp solid was dissolved in dichloromethane
  8. filtrationfiltered through phase
  9. customseparating paper
  10. customthe filtrate evaporated under vacuum
  11. customThe residue was triturated with ether
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-891f0b0c6f49449480cbb5384286bcde
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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