Water → 2-(2-Methylpyrimidin-5-yl)tetrahydrofuran-2-carbonitrile

HRID 512207ノート

反応式

HRID 512207 の反応式
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]=1

参加物

6

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 867162362-(3-Bromopropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile

生成物 1

HCID 867162372-(2-Methylpyrimidin-5-yl)tetrahydrofuran-2-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  1. temperatureto warm to room temperature
  2. extractionextracted with AcOEt (3×15 mL)
  3. washphases were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was used directly for next step without further purification

出典と根拠

ORDレコード
ord-f42b21f4c69e4ba9b1f5bfb2719508cd
出典データセット
uspto-grants-2015_08
特許番号
US09102591B2

反応ノート

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