Reaction equation
[CH3:1][N:2]1[CH2:7][NH:6][C:5](=[N:8][N+:9]([O-:11])=[O:10])[NH:4][CH2:3]1.[H-].[Na+].[Cl:14][C:15]1N=[CH:19][C:18]([CH2:21]Cl)=[CH:17][N:16]=1.O.[CH3:24]N(C)C=O.CN(C=O)C>CN(C=O)C>[Cl:14][C:15]1[CH:24]=[CH:19][C:18]([CH2:21][N:6]2[CH2:7][N:2]([CH3:1])[CH2:3][NH:4][C:5]2=[N:8][N+:9]([O-:11])=[O:10])=[CH:17][N:16]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Methyl-2-nitroimino-hexahydro-1,3,5-triazine (3.0 g) was dissolved in dimethylformamide/DMF (20 ml), followed by portionwise addition of sodium hydride (950 mg: oil free) thereto at a temperature in the range of from 0° to 5° C. After one hour stirring at 0° to 5° C. a solution of 2-chloro-5-chloromethyl-pyrimidine (3.1 g) in 20 ml of DMF was added dropwise to the solution, the temperature was kept constant, followed by a five hour stirring. The reaction mixture thus obtained was poured into iced water, subjected to extraction with methylene chloride a few times and then the extract was dried with anhydrous magnesium sulfate which was removed from the solvent. The thus obtained residue was purified by silica gel column chromatography (eluant: ethanol: chloroform=1: 20), to obtain the desired 1-(2-chloro-5-pyridylmethyl)-5-methyl-2-nitroimino-hexahydro-1,3,5-triazine (3.7 g) having a melting point in the range of from 160° to 161° C.
Workup
- customof from 0° to 5° C
- additionwas added dropwise to the solution
- customThe reaction mixture thus obtained
- extractionsubjected to extraction with methylene chloride a few times
- dry with materialthe extract was dried with anhydrous magnesium sulfate which
- customwas removed from the solvent
- customThe thus obtained residue was purified by silica gel column chromatography (eluant: ethanol: chloroform=1: 20)
Sources & evidence
- ORD record
- ord-4226ff06c93043f4bde3603d05b18598
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719146
Linked notes
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