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

Reaktionsgleichung

Reaktionsgleichung von HRID 1186464
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-21a62a00dcdf4f3c84dfd6684f068520
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

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