Reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[N:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH2:17][CH:16]2[CH3:23])[CH:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[N:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH2:17][CH:16]2[CH3:23])[CH:10]=1)[C:4]#[C:5][CH3:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.08 g of sodium hydride (60% oil suspension) was suspended in 3 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.15 g of 2-butyn-1-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.33 g of 1-(6-chloropyrimidin-4-yl)-2,5-dimethyl hexahydro-1H-azepine at room temperature, and stirred for 4 hours at 60° C. After the reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.17 g of 1-(6-(2-butynyloxy)pyrimidin-4-yl)-2,5-dimethyl hexahydro-1H-azepine (hereinafter, referred to as Compound (34)).
Workup
- stirringstirred for 4 hours at 60° C
- extractionthe mixture was extracted with tert-butyl methyl ether three times
- washThe organic layers were washed with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c90536f9cc424c61a69768863f1a462e
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732448B2
Linked notes
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