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Methanol → HCID 57792030, Verbindung

HRID 421976
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 421976
[C:1]([N:5]1[C:9]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13](Cl)[N:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:19](=[O:22])([O-])[OH:20].[Na+].[CH3:24]O.[C]=O>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CN(C)C=O>[C:1]([N:5]1[C:9]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([C:19]([O:20][CH3:24])=[O:22])[N:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 57792028HCID 57792028, VerbindungHCID 178418416HCID 178418416, Verbindung

Produkt 1

HCID 57792030HCID 57792030, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845
palladium(II) acetate
Katalysator
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Katalysator
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1.93 g of N-(1-tert-butyl-1H-pyrazol-5-yl)-2-chloro-6-methylpyrimidine -4-amine, 328 mg of palladium acetate, 804 mg of 1,1′-bisdiphenylphosphinoferrocene, 920 mg of sodium hydrogen carbonate, 20 ml of methanol and 20 ml of N,N-dimethylformamide was stirred at 100° C. for 16 hours under 3 atmospheric pressure of carbon monoxide, cooled to room temperature, and then diluted with ethyl acetate. An insoluble matter was filtered off using Celite and the resulting ethyl acetate solution was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated. The residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=7/1 to 0/1) to give the title compound.

Aufarbeitung

  1. filtrationAn insoluble matter was filtered off
  2. washthe resulting ethyl acetate solution was washed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=7/1 to 0/1)

Quellen und Nachweise

ORD-Eintrag
ord-32abfa5726ae4214ab0f8062ff04b51e
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08101621B2

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