Water → 2-(2-Methylpyrimidin-5-yl)tetrahydrofuran-2-carbonitrile
Reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][CH:6]([C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)[C:7]#[N:8].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[NH4+].[Cl-].O>C1COCC1>[CH3:15][C:12]1[N:11]=[CH:10][C:9]([C:6]2([C:7]#[N:8])[CH2:2][CH2:3][CH2:4][O:5]2)=[CH:14][N:13]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of 2-(3-bromopropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile (24 mg, 0.089 mmol) in THF (3 mL) was cooled at −78° C. Lithium bis(trimethylsilyl)amide in THF (141 μl, 0, 141 mmol, 1 molar) was added slowly and the mixture was stirred for 1 hour at −78° C. To the reaction mixture was added sat. aq. NH4Cl (10 mL) and the mixture was allowed to warm to room temperature. The reaction mixture was dilluted with H2O (10 mL) and extracted with AcOEt (3×15 mL). The combined org. phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product was used directly for next step without further purification.
Workup
- temperatureto warm to room temperature
- extractionextracted with AcOEt (3×15 mL)
- washphases were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe crude product was used directly for next step without further purification
Sources & evidence
- ORD record
- ord-f42b21f4c69e4ba9b1f5bfb2719508cd
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102591B2
Reaction notes
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