Sodium Carbonate → N-(3-(1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl)-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine

HRID 595156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595156
[CH:1]1([N:7]2[CH:11]=[C:10](B3OC(C)(C)C(C)(C)O3)[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:28]1[CH:29]=[C:30]([NH:35][C:36]2[N:41]=[C:40]([CH:42]([F:44])[F:43])[CH:39]=[CH:38][N:37]=2)[CH:31]=[C:32]([CH3:34])[CH:33]=1>O1CCOCC1>[CH:1]1([N:7]2[CH:11]=[C:10]([C:28]3[CH:29]=[C:30]([NH:35][C:36]4[N:41]=[C:40]([CH:42]([F:43])[F:44])[CH:39]=[CH:38][N:37]=4)[CH:31]=[C:32]([CH3:34])[CH:33]=3)[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 67249363N-(3-bromo-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amineHCID 1222016401-Cyclohex-2-enyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 118208720N-(3-(1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl)-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

1-(Cyclohex-2-en-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (436 mg, 1.59 mmol), sodium carbonate (337 mg, 3.18 mmol), and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (130 mg, 0.159 mmol) were added to a solution of N-(3-bromo-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine (500 mg, 1.59 mmol) in dioxane (7.5 mL). The mixture was purged with nitrogen for 5 minutes and stirred at 110° C. for 18 h. The mixture was allowed to cool to room temperature, diluted with water (30 mL) and extracted with ethyl acetate (3×50 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% EtOAc/hexane) to afford N-(3-(1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl)-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine ESI calc'd. for C21H22F2N5 [M+H]+ 382. found 382.

Aufarbeitung

  1. customThe mixture was purged with nitrogen for 5 minutes
  2. temperatureto cool to room temperature
  3. additiondiluted with water (30 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (0-50% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-befba7af195444ff99153f701a9154da
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242984B2

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