Sodium Carbonate → 4-(5-Methylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde

HRID 1851174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851174
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([NH:14][CH3:15])[N:5]2[CH:16]=[CH:17][N:18]=[C:4]2[N:3]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][NH:14][C:6]1[N:5]2[CH:16]=[CH:17][N:18]=[C:4]2[N:3]=[C:2]([C:24]2[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 866306607-chloro-N-methyl-6-phenylimidazo[1,2-a]pyrimidin-5-amine

Produkt 1

HCID 866306614-(5-Methylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a mixture of 550 mg of the product of step 1 and 350 mg 4-formylphenylboronic acid in 10 mL 1,2-dimethoxyethane, 55 mg tetrakis (triphenylphosphine) palladium(0) and 4 mL of a 10% w/w sodium carbonate solution were added and the resulting mixture was heated by microwave for 2 h. The work up was performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers were dried over sodium sulphate and evaporated. The residue was suspended in ethyl acetate and the resulting mixture was stirred for 2 h at room temperature. The product was collected by filtration and used without further purification.

Aufarbeitung

  1. additionwere added
  2. temperaturethe resulting mixture was heated by microwave for 2 h
  3. customseparating
  4. extractionthe phases and extraction of the aqueous phase with dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulphate
  6. customevaporated
  7. filtrationThe product was collected by filtration
  8. customused without further purification

Quellen und Nachweise

ORD-Eintrag
ord-62c9fede06cf4b7ab184c072acd186ea
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957064B2

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