Cesium fluoride → HCID 68326551, Verbindung

HRID 2359005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2359005
[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11](=[O:15])[NH:12][C:13]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH2:30][CH2:29][CH:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:27][CH:26]=2)O1.[F-].[Cs+]>O1CCOCC1.O.[Cl-].[NH4+]>[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11](=[O:15])[NH:12][C:13]=1[C:34]1[CH2:35][CH2:36][CH:31]([C:28]2[CH:27]=[CH:26][CH:25]=[CH:30][CH:29]=2)[CH2:32][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 25953Cesium fluorideHCID 112890924,4,5,5-Tetramethyl-2-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolaneHCID 23648513HCID 23648513, Verbindung

Produkt 1

HCID 68326551HCID 68326551, VerbindungAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 25517Ammonium ChlorideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 5-benzyl-6-chloro-1H-pyrimidine-2,4-dione (WO06014394) (1.0 g), 4,4,5,5-tetramethyl-2-(4-phenylcyclohex-1-enyl)-[1,3,2]dioxaborolane (1.4 g), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (0.06 g) and cesium fluoride (1.92 g) in 1,4-dioxane (18 mL) and water (2 mL) was heated at 140° C. in a microwave reactor for 20 minutes. The resulting mixture was diluted with saturated aqueous ammonium chloride and filtered to remove the precipitate. The filtrate was extracted with dichloromethane and the combined organic layers washed with water and brine, then dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, eluting with a mixture of methanol and dichloromethane (0:1 to 1:20 by volume) to afford the title compound 2a as an off-white solid (0.48 g). LCMS (Method A): Rt=3.56 min. (M+H)+=359. 1H NMR (DMSO-D6): δ 11.06 (1H, s), 10.69 (1H, s), 7.23-7.21 (10H, m), 5.84-5.79 (1H, m), 3.61 (2H, s), 3.57 (1H, s), 2.77-2.67 (1H, m), 2.19-2.16 (3H, m), 1.84-1.81 (1H, m), 1.68-1.67 (1H, m).

Aufarbeitung

  1. filtrationfiltered
  2. customto remove the precipitate
  3. extractionThe filtrate was extracted with dichloromethane
  4. washthe combined organic layers washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel
  8. washeluting with a mixture of methanol and dichloromethane (0:1 to 1:20 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-4588629fd5e542e386614fb351d06051
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685973B2

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