Methyl iodide → HCID 10236275, Verbindung

HRID 729342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729342
[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]4[C:19]=3[CH:18]=[CH:17][CH:16]=[N:15]4)[CH:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[CH:1]1([N:4]([CH3:22])[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]4[C:19]=3[CH:18]=[CH:17][CH:16]=[N:15]4)[CH:8]=[CH:7][N:6]=2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6918710N-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine

Produkt 1

HCID 10236275HCID 10236275, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-yl-2-pyrimidinamine (25 mg, 0.1 mmol) in DMF (2 mL) was added sodium hydride (6 mg, 0.25 mmol) and methyl iodide (0.013 mL, 0.15 mmol). The reaction was allowed to stir for about 1 hour. The reaction was concentrated in vacuo. Water (10 mL) was added and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were dried (MgSO4) filtered and concentrated in vacuo. The residue was triturated with diethylether to give the title compound as light orange solid (20 mg, 80%). 1H-NMR (400 MHz, CDCl3) δ 9.07 (d, 1H, J=8.8 Hz), 8.46 (s, 1H), 8.35 (m, 2H) 7.12 (dd, 1H, J=8.8, 4.4 Hz), 6.89 (d, 1H, J=5.6 Hz), 3.23 (s, 3H), 2.85 (m, 1H), 0.94 (m, 2H), 0.73 (m, 2H); MS (ESI) (M+H)+ 267.

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. additionWater (10 mL) was added
  3. extractionthe aqueous layer was extracted with EtOAc (2×30 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethylether

Quellen und Nachweise

ORD-Eintrag
ord-66b152ff371c42d3940f9a267d6e1ab9
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582630B2

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