2-(Methylthio)-4-(tributylstannyl)pyrimidine → Methyl-[3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-carbamic acid tert-butyl ester

HRID 1186464

반응식

HRID 1186464 반응식
[CH3:1][S:2][C:3]1[N:8]=[C:7]([Sn](CCCC)(CCCC)CCCC)[CH:6]=[CH:5][N:4]=1.[C:22]([O:26][C:27](=[O:40])[N:28]([C:30]1[C:31]2[N:32]([C:36](Br)=[CH:37][N:38]=2)[CH:33]=[CH:34][N:35]=1)[CH3:29])([CH3:25])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:22]([O:26][C:27](=[O:40])[N:28]([CH3:29])[C:30]1[C:31]2[N:32]([C:36]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=3)=[CH:37][N:38]=2)[CH:33]=[CH:34][N:35]=1)([CH3:25])([CH3:24])[CH3:23]

참가 물질

5

반응물 2

HCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 58818944(3-Bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-carbamic acid tert-butyl ester

생성물 1

HCID 68226929Methyl-[3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 1140Toluene용매

실험 절차

2-Methylsulfanyl-4-tributylstannanyl-pyrimidine (19.1 g, 46.0 mmol) was stirred in degassed toluene (achieved by bubbling nitrogen though solvent for 2 hours) (200 mL) under nitrogen, then (3-bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-carbamic acid tert-butyl ester (13.1 g, 40.0 mmol) (from Example 7 supra) was added followed by bis(triphenylphosphine)palladium (II) chloride (1.12 g, 1.60 mmol) and the reaction was heated at reflux. The reaction was cooled to room temperature and concentrated to dryness. The residue was purified by column chromatography on silica gel (petroleum ether to EtOAc, TLC Rf=0.17, 20% EtOAc in petroleum ether) and then triturated with DIPE to give methyl-[3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-carbamic acid tert-butyl ester. (Yield 8.00 g, 54%).

후처리

  1. temperaturethe reaction was heated
  2. temperatureat reflux
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by column chromatography on silica gel (petroleum ether to EtOAc, TLC Rf=0.17, 20% EtOAc in petroleum ether)
  5. customtriturated with DIPE

출처 및 근거

ORD 기록
ord-21a62a00dcdf4f3c84dfd6684f068520
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673905B2

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