Triphenylphosphine → HCID 45258863, Verbindung

HRID 912199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 912199
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][NH:27][C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[Cl:41][C:42]1[CH:47]=[C:46](I)[CH:45]=[CH:44][N:43]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:41][C:42]1[CH:47]=[C:46]([N:27]2[C:17]3[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=[C:15]([C:12]4[CH:11]=[N:10][C:9]([N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:40][CH:39]=5)[CH2:30][C:31]5[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=5)=[N:14][CH:13]=4)[C:16]=3[CH2:29][CH2:28]2)[CH:45]=[CH:44][N:43]=1

Komponenten

8

Edukt 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 15165112-Chloro-4-iodopyridineHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine

Produkt 1

HCID 45258863HCID 45258863, VerbindungAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (1.65 g, 3.05 mmol) was suspended in dimethylformamide (20 ml), followed by addition of 2-chloro-4-iodopyridine (805 mg, 3.36 mmol), palladium acetate (35 mg, 0.156 mmol), triphenyl phosphine (81 mg, 0.309 mmol) and potassium phosphate (1.95 g, 14.1 mmol), and argon gas was blown for 10 minutes while irradiating ultrasonic wave. The reaction mixture was stirred at 100° C. for 1 hour, and cooled to room temperature, followed by addition of water (50 ml). The mixture was extracted with ethyl acetate (100 ml) and dichloromethane (100 ml), and the combined organic layers were washed with brine, followed by drying over sodium sulfate. After filtering off the drying agent, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=50/1), followed by suspension of the residue in ethyl acetate/hexane (10 ml/50 ml). The precipitate was filtered, and washed with hexane, followed by drying under reduced pressure, to obtain {5-[7-(2-chloro-pyridin-4-yl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl}-bis-(4-methoxy-benzyl)-amine as a yellow powder (1.75 g, 88%).

Aufarbeitung

  1. customwhile irradiating ultrasonic wave
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate (100 ml) and dichloromethane (100 ml)
  4. washthe combined organic layers were washed with brine
  5. dry with materialby drying over sodium sulfate
  6. filtrationAfter filtering off the drying agent
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=50/1)
  9. additionfollowed by suspension of the residue in ethyl acetate/hexane (10 ml/50 ml)
  10. filtrationThe precipitate was filtered
  11. washwashed with hexane
  12. customby drying under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fd55b4ba90e8469da5ba3eb20e4de42e
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022205B2

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