Methanol → Ethyl 4-(1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzoate

HRID 1427460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427460
CO.[C:3]([C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1)(=O)[CH2:4][CH2:5][CH3:6].[F:19][C:20]([F:35])([F:34])[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:32]=[CH:31][C:30]([NH2:33])=[CH:29][N:28]=2)=[CH:23][CH:22]=1.[B][B][B][B][B][B][B][B][B][B]>Cl>[F:35][C:20]([F:19])([F:34])[C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:28]=[CH:29][C:30]([NH:33][CH:3]([C:8]3[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=3)[CH2:4][CH2:5][CH3:6])=[CH:31][N:32]=2)=[CH:25][CH:26]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 431422772-(4-(Trifluoromethyl)phenyl)pyrimidin-5-amineHCID 67980577Ethyl 4-butyrylbenzoateHCID 178419135HCID 178419135, Verbindung

Produkt 1

HCID 67981358Ethyl 4-(1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzoateAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Methanol (0.70 mL) was added to a flask containing ethyl 4-butyrylbenzoate (82.8 mg, 0.376 mmol), 2-(4-(trifluoromethyl)phenyl)pyrimidin-5-amine (90.0 mg, 0.376 mmol) and decaborane (46.0 mg, 0.376 mmol) at room temperature under nitrogen. The resulting solution was stirred at room temperature overnight. The mixture was diluted with 1N HCl and extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-35% ethyl acetate in heptane) gave ethyl 4-(1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzoate (40.0 mg, 24%). 1H NMR (400 MHz, CDCl3, δ): 8.32 (d, J=8.19 Hz, 2H), 8.07 (s, 2H), 7.98-8.04 (m, 2H), 7.63 (d, J=8.19 Hz, 2H), 7.36-7.41 (m, 2H), 4.38-4.43 (m, 2H), 4.35 (q, J=7.02 Hz, 2H), 1.75-1.91 (m, 2H), 1.36 (t, J=7.02 Hz, 3H), 1.20-1.52 (m, 2H), 0.94 (t, J=7.32 Hz, 2H). MS (M+1): 444.3.

Aufarbeitung

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (0-35% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-dd13da270f234283b640820ce642ead6
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933104B2

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