4-sec-Butylphenol → 3-{[4-(1-Methylpropyl)phenoxy]methyl}pyridin-2-amine
Reaction equation
[H-].[Na+].[CH3:3][CH:4]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH2:5][CH3:6].Cl.Cl[CH2:16][C:17]1[C:18]([NH2:23])=[N:19][CH:20]=[CH:21][CH:22]=1>CN(C=O)C>[CH3:3][CH:4]([C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:16][C:17]2[C:18]([NH2:23])=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:11][CH:12]=1)[CH2:5][CH3:6]Participants
Procedure
The solution of (2-aminopyridin-3-yl)methanol (1.0 g) in THF (dry) (10 mL) was added dropwise to a solution of thionyl chloride (0.736 mL) in THF (dry) (30 mL) at 0° C. The mixture was stirred at room temperature for 30 min and concentrated in vacuo to give 3-(chloromethyl)pyridin-2-amine hydrochloride as a yellow gum. NaH (60%, 147 mg) was added to a mixture of 4-(1-methylpropyl)phenol (503 mg) in DMF (dry) (7 mL) at 0° C. The mixture was stirred at the same temperature for 20 min, then was added with the prepared 3-(chloromethyl)pyridin-2-amine hydrochloride (300 mg) at the same temperature. The mixture was stirred at 0° C. for 20 min, room temperature for 1 hr and 60° C. for 1 hr. Silica-gel was added to the mixture and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (151 mg) as pale yellow crystals.
Workup
- stirringThe mixture was stirred at 0° C. for 20 min, room temperature for 1 hr and 60° C. for 1 hr
- additionSilica-gel was added to the mixture
- customthe volatiles were removed in vacuo
- customwas purified by column chromatography (silica gel, eluted with EtOAc in hexane)
Sources & evidence
- ORD record
- ord-551886c62b0f45aca3b5749504889790
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778934B2
Reaction notes
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