Methanol → Ammonium Hydroxide

HRID 1454795

Reaktionsgleichung

Reaktionsgleichung von HRID 1454795
[F:1][C:2]([F:13])([F:12])[C:3]1[N:4]=[C:5]2[CH:10]=[N:9][CH:8]=[CH:7][N:6]2[CH:11]=1.C[OH:15]>[Pd]>[OH-:15].[NH4+:4].[F:12][C:2]([F:1])([F:13])[C:3]1[N:4]=[C:5]2[CH2:10][NH:9][CH2:8][CH2:7][N:6]2[CH:11]=1

Komponenten

5

Edukt 2

HCID 887MethanolHCID 32313062-(Trifluoromethyl)imidazo[1,2-a]pyrazine

Produkt 2

HCID 14923Ammonium HydroxideAusbeute 1 %HCID 147199282-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,2-a]pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

To a solution of 2-(trifluoromethyl)imidazo[1,2-a]pyrazine (2.0 g, 10.46 mmol, from Step A) in methanol (100 mL) was added 10% palladium on carbon (400 mg). The mixture was stirred under atmospheric hydrogen at ambient temperature for 14 h. The mixture was filtered through Celite and washed three times with methanol. The filtrate was concentrated and purified by flash chromatography (silica gel, 10% methanol in ethyl acetate, then 15% methanol in chloroform with 1% aqueous ammonium hydroxide) to give the title compound as a solid. 1H NMR (500 MHz, CDCl3): δ 1.93 (bs, 1H), 3.26 (t, 2H, J=5.5 Hz), 3.99 (t, 2H, J=5.5 Hz), 4.10 (s, 1H), 7.16 (s, 1H). ESI-MS 192 (M+1).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washwashed three times with methanol
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography (silica gel, 10% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5042aaefcc7d45d2ad98a833fcc93fa3
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482336B2

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