Butyl iodide → HCID 13535694, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)=[CH:4][CH:3]=1.[H-].[K+].I[CH2:19][CH2:20][CH2:21][CH3:22]>O1CCCC1>[CH2:19]([N:9]([C:10]1[CH:15]=[N:14][CH:13]=[N:12][CH:11]=1)[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:20][CH2:21][CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2.2 g of N-[(4-chlorophenyl)methyl]-(5-pyrimidyl)amine dissolved in 50 ml of tetrahydrofuran was added 2 g of a 24.6% suspension of potassium hydride in oil. The reaction was allowed to stir at room temperature for approximately 1 hour at which time 2 g of iodobutane was added to the reaction mixture. The mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was dissolved in diethyl ether and the organic phase was washed with water, separated and dried over anhydrous magnesium sulfate. Following concentration of the solution under reduced pressure the residue was chromatographed over silica gel. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford N-butyl-N-[(4-chlorophenyl)methyl]-(5-pyrimidyl)amine as a solid. mp=67°-68° C.
Workup
- additionwas added to the reaction mixture
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in diethyl ether
- washthe organic phase was washed with water
- customseparated
- dry with materialdried over anhydrous magnesium sulfate
- customwas chromatographed over silica gel
- additionFractions containing the major component
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-e46af3dc58704366b0afd0bbd0b210fe
- Source dataset
- uspto-grants-1985_11
- Patent number
- US04552960
Reaction notes
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