Water → Imidazo(1,2-a)pyrazine-3-carbaldehyde
Reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=12.P(Cl)(Cl)(Cl)=O.O.CN([CH:19]=[O:20])C>>[N:1]1[CH:2]=[C:3]([CH:19]=[O:20])[N:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=12Participants
5
Procedure
Imidazo[1,2-a]-pyrazine (0.30 g, 2.5 mmol) was dissolved in anhydrous DMF (10.0 mL) and added to a preformed solution of phosphorous oxychloride (0.26 mL, 2.8 mmol) in anhydrous DMF (10.0 mL). The solution was allowed to stir 72 h under nitrogen at RT. The solution was then poured into water (100 mL) and residual organics extracted with diethyl ether (3×30 mL). The remaining aqueous portion was concentrated to dryness under a nitrogen stream to yield the title compound (0.050 g). MS (ESI+) for m/z 148 (M+H)+.
Workup
- extractionresidual organics extracted with diethyl ether (3×30 mL)
- concentrationThe remaining aqueous portion was concentrated to dryness under a nitrogen stream
Sources & evidence
- ORD record
- ord-827e7449345b4f2d936b529a177db2e8
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07462600B2
Reaction notes
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