2-Butyn-1-ol → 6-(2-Butynyloxy)-4-(trans-2-methylcyclohexyloxy)pyrimidine
Reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([O:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[CH3:22])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[N:10]=[CH:11][N:12]=[C:13]([O:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[CH3:22])[CH:14]=1)[C:4]#[C:5][CH3:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In 1.6 ml of tetrahydrofuran was suspended 0.04 g of sodium hydride (60% in oil), to which 0.4 ml of a tetrahydrofuran solution containing 0.06 g of 2-butyn-1-ol was slowly added dropwise under stirring at room temperature. The mixture was stirred at room temperature for 20 minutes, and 0.4 ml of a tetrahydrofuran solution containing 0.18 g of 4-chloro-6-(trans-2-methylcyclohexyloxy)pyrimidine was slowly added dropwise, followed by stirring at room temperature for 6 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with t-butyl methyl ether. The organic 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 6-(2-butynyloxy)-4-(trans-2-methylcyclohexyloxy)pyrimidine (the present compound (175)).
Workup
- additionwas slowly added dropwise
- stirringThe mixture was stirred at room temperature for 20 minutes
- additionwas slowly added dropwise
- stirringby stirring at room temperature for 6 hours
- extractionextracted three times with t-butyl methyl ether
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0c4bc3ebc07346fabdfd927ca0e3f6e6
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291730B2
Reaction notes
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