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

HRID 1948904Notes

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, (Example 25-5 of in WO01/66099; 10.0 g, 39.6 mmole) was added in portions to a stirred 7N methanolic ammonia solution (220 ml) cooled to 10° C. in an ice/water bath. After stirring for one hour the precipitate was filtered, washed with diethylether and dried thoroughly under high vacuum to give 4-chloro-6-hydroxy-7-methoxyquinazoline (5.65 g, 67.8%); 1H NMR Spectrum: (DMSO d6) 3.96 (s, 3H); 7.25 (s, 1H); 7.31 (s, 1H); 8.68 (s, 1H); Mass Spectrum: (M+H)+ 211

Workup

filtrationwas filtered
washwashed with diethylether
customdried thoroughly under high vacuum

Sources & evidence

ORD record: ord-3a29884cfaee499884369758afb296f2
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399667B2

Reaction notes

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