N-Iodosuccinimide → 8-Chloro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyrazine

HRID 1992424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992424
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([S:11][CH3:12])=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[I:13]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([S:11][CH3:12])=[N:9][C:10]=2[I:13])[CH:5]=[CH:6][N:7]=1

Komponenten

5

Edukt 2

HCID 120273N-IodosuccinimideHCID 591303828-Chloro-3-(methylsulfanyl)imidazo[1,5-A]pyrazine

Produkt 1

HCID 589019878-Chloro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of 8-chloro-3-methylsulfanyl-imidazo[1,5-a]pyrazine (1.75 g, 0.00876 mol) in DMF (15 mL) was added N-iodosuccinimide (3.94 g, 0.0175 mol), the resulting mixture was stirred at 55° C. for 6 h. The mixture was diluted with EtOAc (200 mL), washed with sat. aq. NaHCO3 (40 mL), water (2×40 mL), brine (40 mL), and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography to give the title compound as a yellow solid; 1H NMR (CDCl3, 400 MHz) δ 2.72 (s, 3H), 7.36 (d, J=4.8 Hz, 1H), 7.76 (d, J=4.8 Hz, 1H).

Aufarbeitung

  1. washwashed with sat. aq. NaHCO3 (40 mL), water (2×40 mL), brine (40 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e1fd66b035a74f09b44217c939b32803
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07648987B2

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