tert-Butanol → {2-[1-(2-Fluoroethyl)-1H-imidazol-4-yl]-ethyl}-carbamic Acid Tert-Butyl Ester
Reaction equation
[F:1][CH2:2][CH2:3][N+:4]1[CH:12]=[C:11]2[N:6]([C:7](=[O:13])[NH:8][CH2:9][CH2:10]2)[CH:5]=1.CCN(C(C)C)C(C)C.[C:23]([OH:27])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:7](=[O:13])[NH:8][CH2:9][CH2:10][C:11]1[N:6]=[CH:5][N:4]([CH2:3][CH2:2][F:1])[CH:12]=1)([CH3:26])([CH3:25])[CH3:24]Participants
4
Procedure
To a warmed (30° C.) suspension of 2-(2-fluoro-ethyl)-5-oxo-5,6,7,8-tetrahydro-imidazo[1,5-c]pyrimidin-2-ium (1.01 g, 3.82 mmol) in t-butanol (38 ml), was added Hunig's base (1.33 ml, 7.64 mmol) and the mixture heated to reflux under an inert atmosphere for 1.5 h. The mixture was cooled and the solvent evaporated to a yellow semi-solid, which was triterated with dichloromethane. The solid was filtered off and the filtrate purified by silica column chromatography, to yield a colourless solid (0.384 g, 39%).
Workup
- temperatureTo a warmed
- temperaturethe mixture heated
- temperatureto reflux under an inert atmosphere for 1.5 h
- temperatureThe mixture was cooled
- customthe solvent evaporated to a yellow semi-solid, which
- filtrationThe solid was filtered off
- customthe filtrate purified by silica column chromatography
Sources & evidence
- ORD record
- ord-cf38698c0b614b66b14127fc7c6a06f1
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07754746B2
Reaction notes
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