3-Butyn-2-ol → 4-(1-Methyl-2-propynyloxy)-6-(2-propynyloxy)pyrimidine
Reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:7])[C:5]#[CH:6].Cl[C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]#[CH:18])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:3][CH:4]([O:7][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]#[CH:18])[N:12]=[CH:11][N:10]=1)[C:5]#[CH:6]Participants
Procedure
In 2 ml of tetrahydrofuran was suspended 0.1 g of sodium hydride (60% in oil), to which 0.6 ml of a tetrahydrofuran solution containing 0.12 g of 3-butyn-2-ol was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes and then cooled to 0° C., to which 0.6 ml of a tetrahydrofuran solution containing 0.4 g of 4-chloro-6-(2-propynyloxy)pyrimidine was slowly added dropwise. The mixture was further stirred at 0° C. for 4.5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.14 g of 4-(1-methyl-2-propynyloxy)-6-(2-propynyloxy)pyrimidine (the present compound (11)).
Workup
- additionwas slowly added dropwise
- stirringThe mixture was stirred at room temperature for 20 minutes
- additionwas slowly added dropwise
- stirringThe mixture was further stirred at 0° C. for 4.5 hours
- extractionextracted three times with chloroform
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-899bc5f3909a4aa886bfcd51dc928a46
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06838463B2
Reaction notes
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