Methyl iodide → HCID 81935618, Verbindung

HRID 409456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409456
FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)C[N:7]([C:29]1[N:34]=[CH:33][C:32]([C:35]2[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=2)=[CH:31][N:30]=1)[C@@H]1CN(C2C(CO)=CN=C(N3CCCCC3)N=2)[C@H](CC)C1.CI.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:40][N:38]1[CH:39]=[C:35]([C:32]2[CH:31]=[N:30][C:29]([NH2:7])=[N:34][CH:33]=2)[CH:36]=[N:37]1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59614410HCID 59614410, Verbindung

Produkt 1

HCID 81935618HCID 81935618, VerbindungAusbeute 142,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of [4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-2-piperidin-1-yl-pyrimidin-5-yl]-methanol (40 mg, 0.06 mmol) and methyl iodide (0.004 mL, 0.7 mmol) in 1 mL of DMF is added sodium hydride (2.8 mg, 0.07 mmol) and stirred at room temperature for 1 day. Saturated NH4Cl aqueous solution is added at room temperature and then extracted twice with 50 mL of EtOAc. The combined organic layer is washed with brine, dried over Na2SO4 and concentrated. Column chromatography (eluent: hexane/EtOAc) give (3,5-bis-trifluoromethyl-benzyl)-[3S,5R)-5-ethyl-1-(5-methoxymethyl-2-piperidin-1-yl-pyrimidin-4-yl)-pyrrolidin-3-yl]-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amine (15 mg, 37% yields) as white solid.

Aufarbeitung

  1. extractionextracted twice with 50 mL of EtOAc
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bdf16eaff7824eaeac72c4d9480f2b72
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759365B2

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