Dichloromethane → HCID 69103390, 화합물

HRID 2217254노트

반응식

HRID 2217254 반응식
[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1Br.[C:25]([Si:27]([CH3:30])([CH3:29])[CH3:28])#[CH:26].C(Cl)Cl.CCN(CC)CC>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.[Cu]I.CCOC(C)=O.O>[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1[C:26]#[C:25][Si:27]([CH3:30])([CH3:29])[CH3:28]

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11429076HCID 11429076, 화합물

생성물 1

HCID 69103390HCID 69103390, 화합물수율 71.4%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

To a mixture of 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (500 mg), ethynyl(trimethyl)silane (255 mg), PdCl2(PPh3)2 (46 mg), CuI (12 mg), and CH2Cl2 (10 ml), was added NEt3 (0.2 ml) under ice-bath cooling. The mixture was allowed to warm to 25° C. and stirred for 15 hours. Water and EtOAc were poured into the mixture, and the organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by column chromatography (silica-gel; CH2Cl2—MeOH), recrystallized from EtOH, and dried in vacuo to give 5-{5-amino-3-phenyl-6-[(trimethylsilyl)ethynyl]-2-pyrazinyl}-1-isopropyl-2(1H)-pyridone (373 mg).

후처리

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography (silica-gel; CH2Cl2—MeOH)
  7. customrecrystallized from EtOH
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-3d6bc959d90647bd96d831f161d486d0
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407961B2

반응 노트

불러오는 중…