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Potassium Carbonate → 6-Methoxy-7-(2-piperidinoethoxy)-4-(quinolin-7-yloxy)quinazoline

HRID 454192
Notes
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Reaction equation

HRID 454192 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[CH:35][CH:36]=[N:37]2)=[CH:32][CH:31]=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][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[N:5]=[CH:4][N:3]=[C:2]2[O:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[CH:35][CH:36]=[N:37]2)=[CH:32][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 110885414-Chloro-6-methoxy-7-(2-piperidinoethoxy)quinazolineHCID 1354268667-Hydroxyquinoline

Product 1

HCID 220308846-Methoxy-7-(2-piperidinoethoxy)-4-(quinolin-7-yloxy)quinazolineYield 75%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline (250 mg, 0.78 mmol), (prepared as described for the starting material in Example 180), in DMF (10 ml) was added anhydrous potassium carbonate (320 mg, 2.30 mmol) and 7-hydroxyquinoline (135 mg, 0.94 mmol), and the reaction heated under reflux at 90° C for 1 hour. The reaction was cooled to ambient temperature and 1N aqueous sodium hydroxide added. The resulting precipitate was filtered, washed with water and acetone, and dried under suction to give 6-methoxy-7-(2-piperidinoethoxy)-4-(quinolin-7-yloxy)quinazoline (248 mg, 0.58 mmol, 75%) as a white solid.

Workup

  1. custom(prepared
  2. temperaturethe reaction heated
  3. temperatureThe reaction was cooled to ambient temperature
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water and acetone
  6. customdried under suction

Sources & evidence

ORD record
ord-df3ff9dc71e54087b68120d93b340159
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492560B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes