Ammonium Hydroxide → HCID 178480948, Verbindung

HRID 51538

Reaktionsgleichung

Reaktionsgleichung von HRID 51538
Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C@H:12]3[CH2:17][CH2:16][C@H:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[NH4+:26]>O1CCOCC1>[I:11][C:10]1[C:3]2[C:2]([NH2:26])=[N:7][CH:6]=[N:5][C:4]=2[N:8]([C@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:9]=1

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 178480946HCID 178480946, Verbindung

Produkt 1

HCID 178480948HCID 178480948, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Trans-4-chloro-5-iodo-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidine (0.89 g, 1.9 nmol) in concentrated ammonium hydroxide (40 mL) and dioxane (40 mL) was heated at 120° C. in a pressure vessel for 18 hours. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The water phase was further extracted with ethyl acetate and the combined organic extracts were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to yield trans-5-iodo-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.35 g, 0.8 mmol). RP-HPLC (Hypersil C18, 5 μm, 250×4.6 mm; 25%-100% over 15 min with 0.1 M ammnonium acetate, 1 mL/min) Rt 4.01 min. MS: MH+441.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  3. extractionThe water phase was further extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aeec641f13a74b2baf49f4c6da0d0a94
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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