Methanol → Ammonium Hydroxide

HRID 1454795

Reaction equation

HRID 1454795 reaction equation
[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

Participants

5

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5042aaefcc7d45d2ad98a833fcc93fa3
Source dataset
uspto-grants-2009_01
Patent number
US07482336B2

Linked notes

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