Sodium Carbonate → 4-Furan-2-yl-6-methylsulfanyl-5-vinyl-pyrimidin-2-ylamine

HRID 1355983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1355983
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11](I)=[C:10]([S:13][CH3:14])[N:9]=[C:8]([NH2:15])[N:7]=1.[CH:16]([Sn](CCCC)(CCCC)CCCC)=[CH2:17].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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.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.[Pd]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11]([CH:16]=[CH2:17])=[C:10]([S:13][CH3:14])[N:9]=[C:8]([NH2:15])[N:7]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 81998TributylvinyltinHCID 185075894-Furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine

Produkt 1

HCID 185074684-Furan-2-yl-6-methylsulfanyl-5-vinyl-pyrimidin-2-ylamineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1.00 g (3.00 mmol) 4-furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-yl-amine in 30 ml dioxane under argon at room temperature were added 0.96 ml (3.30 mmol) vinyltributylstannane, 347 mg (0.30 mmol) tetrakis(triphenylphosphine) palladium(O) and 6.0 ml (12.0 mmol) 2M aqueous sodium carbonate solution. The reaction mixture was heated at reflux for 16 h, then cooled to room temperature, 3 g of kieselgel added, and the mixture concentrated in vacuo. Flash chromatography (1/3 ethyl acetate/hexane) followed trituration in ether/hexane afforded 460mg (66%) 4-furan-2-yl-6-methylsulfanyl-5-vinyl-pyrimidin-2-ylamine as an orange crystalline solid. EI-MS m/e (%): 233 (M+, 48), 218 ([M—CH3]+, 76), 216 ([M—NH3]+, 46), 125 (100).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. addition3 g of kieselgel added
  4. concentrationthe mixture concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8c03d03fa4bd4ddb866e8b5291716cb1
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586441B2

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