Tetrahydrofuran → 1-(5-Bromopyrimidin-2-yl)ethan-1-one

HRID 1046102노트

반응식

HRID 1046102 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5](C#N)=[N:6][CH:7]=1.C[Mg+].[Br-].[CH2:13]1[CH2:17][O:16]CC1>>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:17](=[O:16])[CH3:13])=[N:6][CH:7]=1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 6865465-Bromopyrimidine-2-carbonitrileHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 534880641-(5-Bromopyrimidin-2-yl)ethan-1-one수율 30.2%

반응 조건

온도
-78 °C

실험 절차

To a solution of 5-bromopyrimidine-2-carbonitrile (300 mg, 1.63 mmol) in THF (20 mL) was added MeMgBr (5.43 mL, 16.3 mmol) at −78° C. under nitrogen. The solution was stirred at −78° C. for 20 min., quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give an oil, which was purified by prep TLC (3:1 PE/EtOAc) to give 1-(5-bromopyrimidin-2-yl)ethanone (99 mg, yield 30.2%). 1H NMR (CDCl3): δ2.70 (s, 3H), 8.90 (m, 2H).

후처리

  1. customquenched with satd aq NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto give an oil, which
  6. customwas purified by prep TLC (3:1 PE/EtOAc)

출처 및 근거

ORD 기록
ord-d3727f56287c4a5085a760fc8f17c612
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569292B2

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