N-Cyclohexylaniline → (5-Bromo-2-chloro-pyrimidin-4-yl)-cyclohexyl-phenyl-amine

HRID 875945

Reaktionsgleichung

Reaktionsgleichung von HRID 875945
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:10]1([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CN1CCCC1=O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([N:16]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 74567N-CyclohexylanilineHCID 2899735-Bromo-2,4-dichloropyrimidine

Produkt 1

HCID 58299589(5-Bromo-2-chloro-pyrimidin-4-yl)-cyclohexyl-phenyl-amineAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

5-Bromo-2,4-dichloropyrimidine (2.17 ml, 17.14 mmol) and cyclohexyl-phenyl-amine (2.0 g, 11.43 mmol) were dissolved in N-methylpyrrolidone (NMP) (25 ml), and this reaction was heated to 120° C. for 24 hours. The reaction was cooled to room temperature and diluted with ethyl acetate, washed with water and brine. The organic phase was dried using sodium sulfate and concentrated. Purification by flash chromatography (ethyl acetate/hexane) gave compound 37 as a yellow solid (855 mg, 24%). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.27 (1 H, s), 7.41 (3 H, m), 7.21 (2 H, m), 4.62 (1 H, m), 1.93 (2 H, d, J=10 Hz), 1.75 (2 H, d, J=10 Hz), 1.58 (1 H, d, J=10 Hz), 1.34 (2 H, m), 1.15 (2 H, m), 0.91 (1 H, m).

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water and brine
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customPurification by flash chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a85591db25ab4614b9c75c3381179b3d
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980903B2

Verknüpfte Notizen

Wird geladen…