Aniline → 3-(4-Chloro-2-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester

HRID 11792

Reaktionsgleichung

Reaktionsgleichung von HRID 11792
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH2:5][C:6]1[C:7]([Cl:13])=[N:8][C:9](Cl)=[N:10][CH:11]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)C(C)C)(C)C>C(O)CCC.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH2:5][C:6]1[C:7]([Cl:13])=[N:8][C:9]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:10][CH:11]=1

Komponenten

6

Edukt 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 210443123-(2,4-Dichloro-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester

Produkt 1

HCID 210443143-(4-Chloro-2-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-(2,4-dichloro-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (341 mg, 1.0 mmol) (from Example 1d supra) in n-butanol (10 mL) was added aniline (200 mg, 2.15 mmol) (Aldrich) followed by N,N-diisopropylethylamine (258 mg, 2.0 mmol) (Aldrich) and the reaction mixture was heated at 100° C. for 12 hours. After cooling, the reaction mixture was diluted with ethyl acetate (100 mL) and successively washed with saturated aqueous ammonium chloride solution (30 mL), water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel) to give 3-(4-chloro-2-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester. (Yield 45.1 mg, 11.3%).

Aufarbeitung

  1. temperatureAfter cooling
  2. washsuccessively washed with saturated aqueous ammonium chloride solution (30 mL), water (30 mL) and brine (30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-0fc233a13f9f4025aae8312c9520c8fc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098332B2

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