Diethyl (ethoxymethylene)malonate → Ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylate

HRID 714423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714423
Cl.[F:2][C:3]1[CH:4]=[C:5]([C:10](=[NH:16])[NH:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[C:7]([F:9])[CH:8]=1.C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C.[O-]CC.[Na+]>C(O)C>[F:2][C:3]1[CH:4]=[C:5]([C:10]2[N:11]([CH2:12][CH2:13][O:14][CH3:15])[C:20](=[O:19])[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][N:16]=2)[CH:6]=[C:7]([F:9])[CH:8]=1

Komponenten

5

Edukt 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 178495960HCID 178495960, Verbindung2×

Produkt 1

HCID 67955325Ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride (1:1 (i.e. the product from Example 9, Step B) (24.3 mmol) in ethanol (25 mL) was added diethyl ethoxymethylenemalonate (5.25 g, 24.3 mmol) followed by sodium ethoxide (21% soln) (9.1 mL, 24.3 mmol). The reaction mixture was heated and stirred at reflux for 24 h. The reaction mixture was cooled to room temperature concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (6.1 g).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washeluting with 50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d89deebd92c740dc88e3c6509576e898
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187432B2

Notizen zur Reaktion

Wird geladen…