N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide → 1-(5-amino-pyrazin-2-yl)-ethanone O-tert-butyl-oxime
Reaction equation
[C:1]([O:5][N:6]=[C:7]([C:9]1[N:10]=[CH:11][C:12]([NH:15]C(=O)C(C)(C)C)=[N:13][CH:14]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.O.NN.C(OCC)(=O)C>[C:1]([O:5][N:6]=[C:7]([C:9]1[CH:14]=[N:13][C:12]([NH2:15])=[CH:11][N:10]=1)[CH3:8])([CH3:2])([CH3:3])[CH3:4]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
A solution of N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide (563.4 mg, 1.93 mmol) in dioxane (5.8 mL) and hydrazine monohydrate (9.6 mL) was heated under reflux for 48 h. The reaction mixture was allowed to cool to 25° C. and then was diluted with ethyl acetate (100 mL). The organic layer was washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 3/7 ethyl acetate/hexanes) afforded 1-(5-amino-pyrazin-2-yl)-ethanone O-tert-butyl-oxime (408.4 g, quant.) as a light yellow solid: mp 113–115° C.; EI-HRMS m/e calcd for C10H16N4O (M+) 208.1324, found 208.1325.
Workup
- temperatureunder reflux for 48 h
- washThe organic layer was washed with a saturated aqueous sodium chloride solution (1×100 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-698414e486ed4cc899c2fa1774c1054e
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07132425B2
Reaction notes
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