Triphenylphosphine → HCID 86679757, Verbindung

HRID 77468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77468
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[OH:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[NH:39][C:38](=[O:43])[CH:37]=[CH:36]2.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([NH:51][C:52]2[N:57]=[C:56]([CH2:58]O)[CH:55]=[CH:54][N:53]=2)=[CH:47][CH:46]=1>C1COCC1.O>[Cl:44][C:45]1[CH:46]=[CH:47][C:48]([NH:51][C:52]2[N:57]=[C:56]([CH2:58][O:32][C:33]3[CH:34]=[C:35]4[C:40](=[CH:41][CH:42]=3)[NH:39][C:38](=[O:43])[CH:37]=[CH:36]4)[CH:55]=[CH:54][N:53]=2)=[CH:49][CH:50]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 1770652,6-DihydroxyquinolineHCID 5462977Diethyl azodicarboxylateHCID 86679755HCID 86679755, Verbindung

Produkt 1

HCID 86679757HCID 86679757, VerbindungAusbeute 18,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of triphenylphosphine (0.145 g, 0.552 mmol) in THF (2.0 mL) was cooled to 0° C. under N2 and DEAD (0.087 mL, 0.552 mmol) was added dropwise. The mixture was stirred for 10 min, then 6-hydroxyquinolin-2(1H)-one (0.068 g, 0.424 mmol) was added. After stirring for 5 min, a solution of (2-((4-chlorophenyl)amino)pyrimidin-4-yl)methanol (0.1 g, 0.424 mmol) in THF (2.0 mL) was added. The reaction was stirred for 18 h at room temperature. The mixture was diluted with water and filtered. The beige filter cake was stirred in methanol and filtered to give 6-((2-(4-chlorophenylamino)pyrimidin-4-yl)methoxy)quinolin-2(1H)-one as a beige solid (0.03 g, 18%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.70 (s, 1H), 9.91 (s, 1H), 8.53 (d, J=4.8 Hz, 1H), 7.95-7.72 (m, 3H), 7.44-7.16 (m, 5H), 6.98 (d, J=5.0 Hz, 1H), 6.51 (d, J=9.5 Hz, 1H), 5.16 (s, 2H). LCMS: R.T.=3.74; [M+H]+=379.09.

Aufarbeitung

  1. stirringAfter stirring for 5 min
  2. stirringThe reaction was stirred for 18 h at room temperature
  3. filtrationfiltered
  4. stirringThe beige filter cake was stirred in methanol
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-aff0126642e64381ba684ae696814011
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841301B2

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