4-Chloro-7-methoxyquinazolin-6-yl acetate → 4-Chloro-7-methoxyquinazolin-6-ol

HRID 916458Notes

Reaction equation

C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][N:9]=[C:8]2[Cl:17])(=O)C>N>[Cl:17][C:8]1[C:7]2[C:12](=[CH:13][C:14]([O:15][CH3:16])=[C:5]([OH:4])[CH:6]=2)[N:11]=[CH:10][N:9]=1

Participants

Conditions

Temperature: 10 °C

Procedure

6-Acetoxy-4-chloro-7-methoxyquinazoline (10.0 g, 39.6 mmol), (WO 01/04102, Table VI examples), was added in portions to a stirred 7N methanolic ammonia solution (220 ml) and the mixture cooled to 10° C. in an ice/water bath. Initially the solid dissolved to give a yellow solution which then deposited a yellow precipitate. After stirring for one hour the precipitate was filtered off, washed with diethyl ether and dried thoroughly under high vacuum to give 4-chloro-6-hydroxy-7-methoxyquinazoline (5.65 g, 67.8%).

Workup

dissolutionInitially the solid dissolved
customto give a yellow solution which
filtrationwas filtered off
washwashed with diethyl ether
customdried thoroughly under high vacuum

Sources & evidence

ORD record: ord-dabbb77dc4ee4de6a88378da173b268a
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268230B2

Reaction notes

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