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Pyridine → 7-Acetoxy-5-isopropoxy-3,4-dihydroquinazolin-4-one

HRID 639982
Notes
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Reaction equation

HRID 639982 reaction equation
N1C=CC=CC=1.[OH:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:18])[NH:13][CH:14]=[N:15]2)=[C:10]([O:19][CH:20]([CH3:22])[CH3:21])[CH:9]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>O>[C:23]([O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:18])[NH:13][CH:14]=[N:15]2)=[C:10]([O:19][CH:20]([CH3:22])[CH3:21])[CH:9]=1)(=[O:25])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1363551707-hydroxy-5-isopropoxyquinazolin-4(3H)-one

Product 1

HCID 1355107057-Acetoxy-5-isopropoxy-3,4-dihydroquinazolin-4-oneYield 66.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Pyridine (0.18 ml, 1.5 mmol) was added to a suspension of 7-hydroxy-5-isopropoxyquinazolin-4(3H)-one (3.3 g, 15 mmol) in acetic anhydride (10 ml, 75 mmol) and the mixture was stirred at 75° C. for 45 minutes. The mixture was evaporated under reduced pressure and the residue obtained was stirred in water (50 ml) at 75° C. for 1 hour and then cooled to ambient temperature and filtered to afford 5-isopropoxy-4-oxo-3,4-dihydroquinazolin-7-yl acetate (2.6 g, 65% yield) as a white solid:

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue obtained
  3. temperaturecooled to ambient temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8926e283f5a04763b5ff77dae137573d
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07691867B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes