Allyl bromide → N3-Allyl-N4-(1-ethyl-propyl)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine
Reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:35](Br)[CH:36]=[CH2:37]>C1COCC1>[CH2:37]([NH:24][C:8]1[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])=[N:10][C:11]([CH3:13])=[CH:12][C:7]=1[NH:6][CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:36]=[CH2:35]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of N4-(1-ethyl-propyl)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine (500 mg, 1.52 mmol) in dry THF was added 1M in THF of lithium bis(trimethylsilyl)amide (1.6 ml, 1.6 mmol) at −78° C., After stirring at −78° C. for 10 min, allyl bromide (0.13 ml, 1.52 mmol) was added and the resulting mixture was stirred at that temperature for 20 min, then warmed to room temperature overnight. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound as a green-blue oil. The oil was purified through silica gel column chromatography using 5% ethyl acetate in hexane as eluent to give a yellow crystal, mp. 86–88° C.
Workup
- stirringthe resulting mixture was stirred at that temperature for 20 min
- temperaturewarmed to room temperature overnight
- customThe mixture was quenched with water
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-24941f368b0947fd8090bc2496b932a1
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07125880B1
Reaction notes
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