Sodium Carbonate → 2-(2,6-Dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methoxy-6-methylpyrimidine

HRID 1091953

Reaktionsgleichung

Reaktionsgleichung von HRID 1091953
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[CH:15]=[CH:14][C:13]=2[CH3:21])=[C:4]([CH3:22])[N:3]=1.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[CH:15]=[CH:14][C:13]=2[CH3:21])=[C:4]([CH3:22])[N:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 5833222,6-Dimethylphenylboronic acidHCID 575314062-Chloro-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methoxy-6-methylpyrimidine

Produkt 1

HCID 575314972-(2,6-Dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methoxy-6-methylpyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture containing 2-chloro-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methoxy-6-methylpyrimidine (˜3.91 mmol), 2,6-dimethylphenylboronic acid (1.17 g, 7.82 mmol), 15.6 mL of 1 M aqueous sodium carbonate and dioxane (56 mL) is degassed by bubbling with argon for 20 min. To this mixture is added Pd(PPh3)4 (226 mg, 0.05 mol %). The resulting yellow mixture is heated at 90° C. under nitrogen with magnetic stirring for 24 h. Another 50 mg of Pd(PPh3)4 is added and heating is continued for another 18 h until the reaction is complete by LC/MS analysis. The reaction mixture is allowed to cool to ambient temperature and partitioned between EtOAc (200 mL) and water (70 mL). The organic layer is separated, extracted with water (70 mL×2), brine (70 mL), dried over anhydrous sodium sulfate, filtered and evaporated to obtain a yellow oil. Purification by chromatography on silica gel (5-50% EtOAc/Hexanes) provides the title compound as a colorless solid. LC-MS found 391.4 (MH+), rt=1.93 min.

Aufarbeitung

  1. customis degassed
  2. customby bubbling with argon for 20 min
  3. additionTo this mixture is added Pd(PPh3)4 (226 mg, 0.05 mol %)
  4. additionAnother 50 mg of Pd(PPh3)4 is added
  5. temperatureheating
  6. waitis continued for another 18 h until the reaction
  7. temperatureto cool to ambient temperature
  8. custompartitioned between EtOAc (200 mL) and water (70 mL)
  9. customThe organic layer is separated
  10. extractionextracted with water (70 mL×2), brine (70 mL)
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customevaporated
  14. customto obtain a yellow oil
  15. customPurification by chromatography on silica gel (5-50% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-dd4059a6d07d47cf99d8be58b6d966fe
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129395B2

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