2-Butyn-1-ol → 4-(2-Butyn-1-yloxy)-6-isopropoxypyrimidine
Reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([O:15][CH:16]([CH3:18])[CH3:17])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:14]=[C:13]([O:15][CH:16]([CH3:18])[CH3:17])[N:12]=[CH:11][N:10]=1)[C:4]#[C:5][CH3:6]Participants
Procedure
In 0.5 ml of tetrahydrofuran was suspended 0.02 g of sodium hydride (60% in oil), to which 0.1 ml of a solution containing 0.02 g of 2-butyn-1-ol in tetrahydrofuran was added dropwise at room temperature. After stirring at room temperature for 20 minutes, 0.1 ml of a solution containing 0.05 g of 4-chloro-6-(isopropyloxy)pyrimidine in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 2 hours. The mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. 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 0.05 g of 4-(2-butynyloxy)-6-isopropoxypyrimidine (the present compound (1)).
Workup
- additionwas added dropwise at room temperature
- additionwas added dropwise at room temperature
- stirringby stirring for 2 hours
- extractionwas extracted three times with t-butyl methyl ether
- 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-0ed5a478e559434db53f87c5a7571715
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223769B2
Reaction notes
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