(+-)-2-Butanol → HCID 17979117, compound
Reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[C:8](Cl)[N:7]=[CH:6][N:5]=1.[CH2:11]([OH:15])[C:12]#[C:13][CH3:14].[Cl-].[NH4+].[CH3:18][CH:19]([OH:22])[CH2:20][CH3:21]>O1CCCC1>[CH:19]([O:22][C:4]1[CH:9]=[C:8]([O:15][CH2:11][C:12]#[C:13][CH3:14])[N:7]=[CH:6][N:5]=1)([CH2:20][CH3:21])[CH3:18]Participants
Procedure
In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.17 g of 2-butanol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 3 hours. To this was added dropwise 0.4 ml of a solution containing 0.18 g of 2-butyn-1-ol in tetrahydrofuran and further added 0.10 g of sodium hydride (60% in oil), followed by stirring at room temperature for 7 hours. The reaction 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 0.31 g of 4-(sec-butyloxy)-6-(2-butynyloxy)pyrimidine (the present compound (23)).
Workup
- additionwas added dropwise at 0° C.
- stirringby stirring at the same temperature for 3 hours
- stirringby stirring at room temperature for 7 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-dff7dc32aeff4df7a7516e75195f636f
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223769B2
Reaction notes
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