Water → HCID 178503530, Verbindung

HRID 230188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230188
[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([CH2:7]CO)[CH2:4][O:3]1.[H-].[Na+].Cl[C:14]1[N:19]=[C:18]([S:20][CH3:21])[N:17]=[C:16]2[NH:22][N:23]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])[C:15]=12.[OH2:32]>O1CCOCC1.C(OCC)(=O)C>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:24]1[C:15]2[C:16](=[N:17][C:18]([S:20][CH3:21])=[N:19][C:14]=2[O:32][CH2:7][CH:5]2[CH2:4][O:3][C:2]([CH3:1])([CH3:10])[O:6]2)[NH:22][N:23]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11480522(4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolaneHCID 178503465HCID 178503465, Verbindung

Produkt 1

HCID 178503530HCID 178503530, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To (R)-2,2-dimethyl-1,3-dioxolane-4-ethanol (2.12 g) in 10 mL dioxane was added sodium hydride (0.656 g) at 0° C. The resulting mixture was stirred for 10 minutes, and then 4-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine (1.0 g, 3.213 mmol) was added. The reaction mixture was heated to reflux for one hour, then cooled to room temperature. Water (150 mL) and ethyl acetate (300 mL) was added, and the layers separated. The aqueous layer was washed four times with ethyl acetate, and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (20% to 30% EtOAc in hexanes) to yield 1.03 g of 3-(2-Chloro-phenyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine. Mass Spec. M+H=407. Mp.=119.5-122.3° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for one hour
  3. customthe layers separated
  4. washThe aqueous layer was washed four times with ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (20% to 30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c1142b5e1ae746e197ec0655a3748101
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566708B2

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