Hydrochloric Acid → 2-(2-oxopyrimidin-1(2H)-yl)propanoic acid

HRID 243674

Reaktionsgleichung

Reaktionsgleichung von HRID 243674
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]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 6422322-Bromopropionic acid, (S)-HCID 178479648HCID 178479648, Verbindung

Produkt 1

HCID 167812472-(2-oxopyrimidin-1(2H)-yl)propanoic acid

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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 cooled down to ambient temperature, it 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).

Aufarbeitung

  1. temperatureAfter cooled down to ambient temperature
  2. 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)
  3. customRemoval of the volatiles in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3eaf5b0e797b4888a9fdac6a8950be13
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653260B2

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