Chloroacetic Acid → 2-(6-Oxo-1,6-dihydropyrimidin-1-yl)acetic acid

HRID 243675

Reaktionsgleichung

Reaktionsgleichung von HRID 243675
[N:1]1[CH:6]=[CH:5][C:4](=[O:7])[NH:3][CH:2]=1.[OH-].[Na+].Cl[CH2:11][C:12]([OH:14])=[O:13].Cl>>[O:7]=[C:4]1[N:3]([CH2:11][C:12]([OH:14])=[O:13])[CH:2]=[N:1][CH:6]=[CH:5]1

Komponenten

5

Edukt 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 206954-Hydroxypyrimidine

Produkt 1

HCID 223416992-(6-Oxo-1,6-dihydropyrimidin-1-yl)acetic acid

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To pyrimidin-4(3H)-one (0.608 g, 6.33 mmol) was added 5 N sodium hydroxide solution (2.5 mL) followed by chloroacetic acid (0.598 g, 6.33 mmol). The reaction mixture was heated at 105° C. for 2 h. After cooled down to ambient temperature, it was neutralized with 2 N hydrochloric acid (3.2 mL) and then directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 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. 1H NMR (DMSO-d6): δ 13.2 (s, 1H), 8.43 (s, 1H), 7.94 (d, J=6.7 Hz, 1H), 6.43 (d, J=6.6 Hz, 1H), 4.63 (s, 2H). LC/MS 155.1 (M+1).

Aufarbeitung

  1. temperatureAfter cooled down to ambient temperature
  2. customdirectly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 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-325d43bc0319462a90b33d48a2d9b474
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653260B2

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