Potassium Carbonate → HCID 22030610, compound

HRID 1791718Notes

Reaction equation

HRID 1791718 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:28][C:29]1[CH:38]=[C:37]2[C:32]([CH:33]=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1.[OH-].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:28][C:29]3[CH:38]=[C:37]4[C:32]([CH:33]=[CH:34][CH:35]=[N:36]4)=[CH:31][CH:30]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazolineHCID 1354268667-Hydroxyquinoline

Product 1

HCID 22030610HCID 22030610, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 7-benzyloxy-4-chloro-6-methoxyquinazoline (1.82 g, 6.1 mmol), (prepared as described for the starting material in Example 1), in DMF (50 ml) was added potassium carbonate (2.50 g, 18.1 mmol) and 7-hydroxyquinoline (1.06 g, 7.3 mmol), and the reaction heated under reflux at 90C for 4 hours. The reaction was poured into 1N aqueous sodium hydroxide and the resulting precipitate filtered, washed with water, and dried under suction. Further drying in a vacuum oven gave 7-benzyloxy-6-methoxy-4-(quinolin-7-yloxy)quinazoline (1.50 g, 3.7 mmol, 60%) as a cream solid.

Workup

  1. custom(prepared
  2. temperaturethe reaction heated
  3. filtrationthe resulting precipitate filtered
  4. washwashed with water
  5. customdried under suction
  6. customFurther drying in a vacuum oven

Sources & evidence

ORD record
ord-b2c124acdf06481b890ccc98250d1680
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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