Water → 7-Acetoxy-6-methoxy-3,4-dihydroquinazolin-4-one
Reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:13][CH3:14].[C:15](OC(=O)C)(=[O:17])[CH3:16].O>N1C=CC=CC=1>[C:15]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:13][CH3:14])(=[O:17])[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 7-hydroxy-6-methoxyquinazolin-4-(3H)-one (8.0 g, 41.6 mmol), pyridine (7.5 ml) and acetic anhydride (63 ml) was heated at 100° C. for 4.5 hours and left to cool to ambient temperature 18 hours. The reaction mixture was poured into ice/water (400 ml) and the resultant precipitate collected by filtration and dried in vacuo. Analysis revealed that hydrolysis of the acetate group on the 4 position of the quinazoline was incomplete. The mixture was therefore treated with water (150 ml) and pyridine (0.5 ml) at 90° C. for 15 minutes. The reaction was cooled and the solid was collected by filtration, washed with water and dried in vacuo to yield 7-(acetoxy)-6-methoxyquinazolin-4-(3H)-one (7.4 g, 76% yield):
Workup
- waitleft
- temperatureto cool to ambient temperature 18 hours
- filtrationthe resultant precipitate collected by filtration
- customdried in vacuo
- customAnalysis revealed that hydrolysis of the acetate group on the 4 position of the quinazoline
- temperatureThe reaction was cooled
- filtrationthe solid was collected by filtration
- washwashed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-6bd0b80e7136444ebdd6f32f5915298b
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691867B2
Reaction notes
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