2-Butyn-1-ol → HCID 17979111, compound
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]([O:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[CH:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:10]=[C:11]([O:15][CH2:16][C:17]([OH:19])([CH3:18])[CH3:20])[N:12]=[CH:13][N:14]=1)[C:4]#[C:5][CH3:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In 6 ml of tetrahydrofuran was suspended 0.29 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.25 g of 2-butyn-1-ol in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.66 g of 1-(6-chloropyrimidin-4-yloxy)-2-methyl-2-propanol in tetrahydrofuran at 0° C., followed by increasing the temperature up to room temperature and stirring for 5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.33 g of 4-(2-butynyloxy)-6-(2-hydroxy-2-methylpropyloxy)pyrimidine.
Workup
- additionwas added dropwise at room temperature
- stirringstirring for 5 hours
- extractionwas extracted three times with ethyl acetate
- washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a6eefc78f00b474787dc2479398ed99a
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223769B2
Reaction notes
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