Urea → Methyl 4-(4-fluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 227707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227707
[CH3:1][O:2][CH2:3][C:4](=O)[CH2:5][C:6]([O:8][CH3:9])=[O:7].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[NH2:20][C:21]([NH2:23])=[O:22].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C1(C)C=CC=CC=1.O>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:3][O:2][CH3:1])[NH:23][C:21](=[O:22])[NH:20]2)=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 1176UreaHCID 680234-FluorobenzaldehydeHCID 123500Methyl 4-methoxyacetoacetateHCID 2733225Ytterbium triflate

Produkt 1

HCID 53439029Methyl 4-(4-fluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Methyl 4-(methyloxy)-3-oxobutanoate (2.0 g, 13.69 mmol, 1 equiv), 4-Fluorobenzaldehyde (1.7 g, 13.69 mmol, 1 equiv), urea (1.64 g, 27.34 mmol, 2 equiv), and ytterbium triflate (854 mg, 1.37 mmol, 0.1 equiv) were combined in Toluene (3 mL) and heated to 100° C. in a sealed tube for three hours. The residue was diluted with 10 mL of water and extracted with EtOAc (10 mL). The organic layer was washed with brine and concentrated en vacuo to yield 4.03 g of the title compound as a light yellow oil (100%). MS (ES+) m/e 295 [M+H]+

Aufarbeitung

  1. extractionextracted with EtOAc (10 mL)
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated en vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fa72a0ad3f224cd894286aa0c4c2f465
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560467B2

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