Benzaldehyde → 4-(4-bromophenyl)-2,6-diphenylpyrimidine
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=O.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CI.C[O-].[Na+].CO.Cl.[C:27]([NH2:35])(=[NH:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH-].[Na+]>C(O)C>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]2[CH:1]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:35]=[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:34]=2)=[CH:5][CH:6]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Bromoacetophenone 19.9 g (100 mmol) and benzaldehyde 10.6 g (100 mmol) were mixed and, the system was substituted with argon. Next, 200 mL of ethanol and 10 MeI of a 1N sodium methoxide/methanol solution were added thereto and stirred at room temperature for 5 hours. Thereafter, the solution was heated on an oil bath of 70° C. to carry out reaction for further 4 hours while refluxing ethanol. Then, benzamidine hydrochloride 9.40 g (60 mmol) and sodium hydroxide 8.00 g (200 mmol) were added thereto and heated on the oil bath of 70° to carry out reaction for 5 hours. After finishing the Reactions the deposit was separated by filtering and refined by silica gel chromatography to obtain 13.6 g (yield: 35%) of 4-(4-bromophenyl)-2,6-diphenylpyrimidine.
Workup
- temperatureThereafter, the solution was heated on an oil bath of 70° C.
- customreaction for further 4 hours
- temperatureheated on the oil bath of 70°
- customreaction for 5 hours
- customwas separated
- filtrationby filtering
Sources & evidence
- ORD record
- ord-8fe8d6c4d6274c5cabc239c17447df25
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217570B2
Reaction notes
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