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

HRID 454192Notes

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

Participants

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

custom(prepared
temperaturethe reaction heated
temperatureThe reaction was cooled to ambient temperature
filtrationThe resulting precipitate was filtered
washwashed with water and acetone
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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