3-Hydroxybenzaldehyde → 2-Chloroquinazolin-4(3H)-one
Reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Cl:10][C:11]1[N:16]=CC=C[N:12]=1.CCN(C(C)C)C(C)C>CCOC(C)=O>[Cl:10][C:11]1[NH:16][C:5](=[O:6])[C:4]2[C:3](=[CH:2][CH:9]=[CH:8][CH:7]=2)[N:12]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
A mixture of 3-hydroxybenzaldehyde (2.00 g, 16.38 mmol), 2-chloropyrimidine (1.88 g, 16.38 mmol) and iPr2NEt (5.71 mL, 32.75 mmol), under N2 atmosphere was heated at 105° C. for 24 h. The reaction mixture was allowed to cool to room temperature. The crude was subjected to column chromatography (silica gel, 20% EtOAc in hexanes) to furnish 1.62 g of the desired aryl ether (1) as an off-white solid.
Workup
- temperatureto cool to room temperature
Sources & evidence
- ORD record
- ord-d571463cc058402892e08dad215deb4e
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07244738B2
Reaction notes
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