Trimethylaluminum → 1-(1-Ethylpropyl)-5-methyl-3-(methylthio)-2 (1H)-pyrazinone

HRID 1271139노트

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HRID 1271139 반응식
Br[C:2]1[N:3]=[C:4]([S:14][CH3:15])[C:5](=[O:13])[N:6]([CH:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:7]=1.[CH3:16][Al](C)C>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:9]([CH:8]([N:6]1[CH:7]=[C:2]([CH3:16])[N:3]=[C:4]([S:14][CH3:15])[C:5]1=[O:13])[CH2:11][CH3:12])[CH3:10]

참가 물질

5

반응물 2

HCID 16682925TrimethylaluminumHCID 588451705-bromo-1-(1-ethylpropyl)-3-(methylthio)-2 (1H)-pyrazinone

생성물 1

HCID 588451711-(1-Ethylpropyl)-5-methyl-3-(methylthio)-2 (1H)-pyrazinone수율 73%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of XXXI (2.0 g, 6.9 mmol) and dichlorobis(triphenylphosphine)palladium(II) (484 mg, 0.7 mmol) in THF (40 mL) was treated with trimethylaluminum (6.2 mL, 12.4 mmol, 2M/toluene) dropwise at 0° C. The reaction was refluxed for 4 h, cooled to 0° C. quenched with water (50 mL) and extracted with ethyl acetate (100 mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo to give crude residue. Purification by flash column chromatography (silica, ethyl acetate:hexane 1:1) gave the product XXXII (1.14 g, 73%) as a pale yellow solid.

후처리

  1. temperatureThe reaction was refluxed for 4 h
  2. customquenched with water (50 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give crude residue
  8. customPurification by flash column chromatography (silica, ethyl acetate:hexane 1:1)

출처 및 근거

ORD 기록
ord-ccc4162a353a4721ab0d609bf5855f22
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205306B2

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