Cesium carbonate → 4-Chloro-6-{2,2,2-trifluoro-1-[2-(4-methyl-thiophen-3-yl)-phenyl]-ethoxy}-pyrimidin-2-ylamine

HRID 1620817

Reaktionsgleichung

Reaktionsgleichung von HRID 1620817
[F:1][C:2]([F:18])([F:17])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:15]([CH3:16])=[CH:14][S:13][CH:12]=1)[OH:4].[NH2:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[C:22]([Cl:27])[N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C(OCC)(=O)C>[Cl:27][C:22]1[CH:23]=[C:24]([O:4][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:11]2[C:15]([CH3:16])=[CH:14][S:13][CH:12]=2)[C:2]([F:1])([F:17])[F:18])[N:25]=[C:20]([NH2:19])[N:21]=1

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 655222-Amino-4,6-dichloropyrimidineHCID 667434372,2,2-Trifluoro-1-[2-(4-methyl-thiophen-3-yl)-phenyl]-ethanol

Produkt 1

HCID 866210844-Chloro-6-{2,2,2-trifluoro-1-[2-(4-methyl-thiophen-3-yl)-phenyl]-ethoxy}-pyrimidin-2-ylamineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 2,2,2-trifluoro-1-[2-(4-methyl-thiophen-3-yl)-phenyl]-ethanol (100 mg, 0.37 mmol), 2-amino-4,6-dichloro-pyrimidine (54 mg, 0.33 mmol), cesium carbonate (481 mg, 1.48 mmol) and 1,4-dioxane (1 ml) was heated at 110° C. overnight. The reaction mixture was cooled to room temperature; 10 ml of ethyl acetate was added. The mixture was then filtered through Celite, the filtrate was concentrated to give 100 mg of 4-chloro-6-{2,2,2-trifluoro-1-[2-(4-methyl-thiophen-3-yl)-phenyl]-ethoxy}-pyrimidin-2-ylamine, yield: 76%.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe mixture was then filtered through Celite
  3. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6484e83dcb734bb2a7021b34a770b029
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772482B2

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