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

HRID 1482495

반응식

HRID 1482495 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 178418573HCID 178418573, 화합물

생성물 1

HCID 534880641-(5-Bromopyrimidin-2-yl)ethan-1-one

반응 조건

온도
-78 °C

실험 절차

To a solution of 5-bromopyrimidine-2-carbonitrile (221 mg, 1.2 mmol) in THF (10 ml) was added methylmagnesium bromide (3.0 ml, 4.20 mmol, 1.4 molar, THF) at −78 CC under nitrogen. The solution was stirred at −78° C. for 3.5 hours, and then quenched with satd aq NH2Cl, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated. The reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1) to afford 1-(5-bromopyrimidin-2-yl)ethanone (1.55 mg, 61.% yield). 1H NMR (CDCl3 500 MHz): δ 9.00 (s, 2H), 2.80 (s, 3H).

후처리

  1. customquenched with satd aq NH2Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1)

출처 및 근거

ORD 기록
ord-d40aaadb862d4059abe3fab291e05307
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09415055B2

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