Diethyl oxalacetate → Ethyl 2-amino-6-oxo-3,6-dihydropyrimidine-4-carboxylate

HRID 7635

Reaktionsgleichung

Reaktionsgleichung von HRID 7635
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]([C:8](OCC)=[O:9])=O)[CH3:2].C(=O)(O)O.[NH2:18][C:19]([NH2:21])=[NH:20]>C(O)C.O>[CH2:1]([O:3][C:4]([C:5]1[N:18]=[C:19]([NH2:21])[NH:20][C:8](=[O:9])[CH:6]=1)=[O:13])[CH3:2]

Komponenten

5

Edukt 2

HCID 66951Diethyl oxalacetateHCID 286947Carbonic acid-guanidine (1:1)

Produkt 1

HCID 135449811Ethyl 2-amino-6-oxo-3,6-dihydropyrimidine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of oxalacetic acid diethyl ester (8.5 g, 45.2 mmol) in ethanol (100 mL) was treated with guanidine carbonate (8.1 g, 45.2 mmol) and this was stirred under reflux for 2 hours. The mixture was diluted with water, concentrated to removed ethanol, and the solid was collected by filtration. The solid was then suspended in ethanol (40 mL) and concentrated hydrochloric acid (1 mL) and refluxed for 15 minutes. The mixture was then cooled, basified with potassium carbonate, diluted with water and concentrated to removed ethanol. The white solid was collected by filtration and vacuum dried to give J1.1 (1.67 g, 20%). 1H-NMR (DMSO-d6) δ: 10.34 (1H, br s), 8.92 (1H, br s), 7.46 (1H, br, s), 5.42 (1H, s), 4.18 (2H, q, J=7 Hz), 1.24 (3H, t, J=7 Hz).

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. concentrationconcentrated
  3. customto removed ethanol
  4. filtrationthe solid was collected by filtration
  5. temperatureconcentrated hydrochloric acid (1 mL) and refluxed for 15 minutes
  6. temperatureThe mixture was then cooled
  7. additiondiluted with water
  8. concentrationconcentrated
  9. customto removed ethanol
  10. filtrationThe white solid was collected by filtration and vacuum
  11. customdried
  12. customto give J1.1 (1.67 g, 20%)

Quellen und Nachweise

ORD-Eintrag
ord-764d1c4e0aa144ca945e165640b2174a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087614B2

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