Hydrochloric Acid → 2-(2-oxopyrimidin-1(2H)-yl)propanoic acid
Reaction equation
Cl.[OH:2][C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[OH-].[Na+].Br[C@@H:12]([CH3:16])[C:13]([OH:15])=[O:14].Cl>>[O:2]=[C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]1[CH:12]([CH3:16])[C:13]([OH:15])=[O:14]Participants
5
Conditions
- Temperature
- 80 °C
Procedure
To 2-hydroxypyrimidine hydrochloride (1.27 g, 9.54 mmol) was added 5 N sodium hydroxide solution (5.7 ml) followed by (2S)-2-bromopropanoic acid (0.95 ml, 11 mmol). The reaction mixture was heated at 80° C. for 4 h. After cooling to ambient temperature, the reaction was neutralized with 2N hydrochloric acid (4.8 ml) and then directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-50% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). Removal of the volatiles in vacuo afforded the title compound as a white solid. LC/MS 169.1 (M+1)+.
Workup
- temperatureAfter cooling to ambient temperature
- customdirectly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-50% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)
- customRemoval of the volatiles in vacuo
Sources & evidence
- ORD record
- ord-9af29d949bc74b06acef709bb91a2b20
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501786B2
Reaction notes
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