Dimethylamine → 6-chloro-N,N-dimethyl-5-nitropyrimidin-4-amine
Reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[CH3:17][NH:18][CH3:19]>CC(C)=O>[Cl:11][C:6]1[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([N:18]([CH3:19])[CH3:17])[N:3]=[CH:4][N:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
To a mixture of 7.76 g of 4, 6-dichloro-5-nitropyrimidine, 3.70 g of sodium hydrogencarbonate and 80 ml of acetone was gradually dropwise added 50% aqueous dimethylamine (3.79 g) with ice cooling and stirring, and the mixture was stirred at room temperature for 30 minutes. Every 30 minutes, 50% aqueous dimethylamine (0.7 g) was added three times to the mixture, and the solvent was evaporated in vacuo. The residue was mixed with 70 ml of ethyl acetate, heated at 45° C. and the insoluble material was filtered off. The filtrate was dried over anhydrous sodium sulfate and the solvent evaporated. The residue was mixed with n-hexane and triturated. The precipitated crystals were filtered off to give 7.53 g of 4-chloro-6-dimethylamino-5-nitropyrimidine.
Workup
- stirringthe mixture was stirred at room temperature for 30 minutes
- customthe solvent was evaporated in vacuo
- additionThe residue was mixed with 70 ml of ethyl acetate
- filtrationthe insoluble material was filtered off
- dry with materialThe filtrate was dried over anhydrous sodium sulfate
- customthe solvent evaporated
- additionThe residue was mixed with n-hexane
- customtriturated
- filtrationThe precipitated crystals were filtered off
Sources & evidence
- ORD record
- ord-940bf8819deb47bf95841a41448820dd
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05442060
Reaction notes
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