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

HRID 512207노트

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HRID 512207 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f42b21f4c69e4ba9b1f5bfb2719508cd
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102591B2

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