Potassium Carbonate → 3-(4-methoxybenzyl)-1-benzyl-6-chloro-3,4-dihydroquinazolin-2(1H)-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2Br)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:26]([N:33]=[C:34]=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH2:9][C:10]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:16])[CH:15]=3)[N:33]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:34]2=[O:35])=[CH:5][CH:4]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
To a stirring mixture of N-(4-methoxybenzyl)(2-bromo-5-chlorophenyl)methanamine (0.94 g, 2.77 mmol), Pd(PPh3)4 (0.32 g, 0.277 mmol), and K2CO3 (0.77 g, 5.55 mmol) was added DMF (5.0 mL), followed by slow addition of benzyl isocyanate (0.38 mL, 3.05 mmol) at 0° C. The mixture was heated at 120° C. for 4 hrs. The resulting mixture was concentrated and passed through a short path of silica gel and eluted with DCM until the product eluted. The combined organic layers were concentrated to give the product 3-(4-methoxybenzyl)-1-benzyl-6-chloro-3,4-dihydroquinazolin-2(1H)-one as a pale yellow foam. MS m/e 340 (M+H)+.
Workup
- concentrationThe resulting mixture was concentrated
- washeluted with DCM until the product
- washeluted
- concentrationThe combined organic layers were concentrated
Sources & evidence
- ORD record
- ord-3745554f7bb44bcd8985aa7ec01b93b3
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935709B2
Reaction notes
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