Malonic Acid → 1-(4-Bromo-phenyl)-3-cyclopropyl-pyrimidine-2,4,6-trione

HRID 2224152

Reaktionsgleichung

Reaktionsgleichung von HRID 2224152
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH:12]2[CH2:14][CH2:13]2)=[O:10])=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.[C:22](O)(=[O:27])[CH2:23][C:24](O)=[O:25]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:24](=[O:25])[CH2:23][C:22](=[O:27])[N:11]([CH:12]3[CH2:13][CH2:14]3)[C:9]2=[O:10])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 867Malonic AcidHCID 7918Acetic AnhydrideHCID 458603331-(4-Bromophenyl)-3-cyclopropylurea

Produkt 1

HCID 597170511-(4-Bromo-phenyl)-3-cyclopropyl-pyrimidine-2,4,6-trioneAusbeute 73 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 1-(4-bromo-phenyl)-3-cyclopropyl-urea 31 (12.9 g) obtained in Step 1 was added acetic anhydride (25.8 ml), malonic acid 4 (5.79 g) was added under a nitrogen atmosphere, and the mixture was stirred at 100° C. for 3 hrs. After allowing to cool to room temperature, the reaction mixture was concentrated under reduced pressure. Diethyl ether-ethanol [4:1 (volume ratio), 100 ml] was added to the residue and, after stirring, the crystals were collected by filtration and dried to give 1-(4-bromo-phenyl)-3-cyclopropyl-pyrimidine-2,4,6-trione 32 (11.9 g, yield 73%) as pale-yellow crystals.

Aufarbeitung

  1. additionwas added under a nitrogen atmosphere
  2. temperatureto cool to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionDiethyl ether-ethanol [4:1 (volume ratio), 100 ml] was added to the residue
  5. stirringafter stirring
  6. filtrationthe crystals were collected by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-eeea6b0b171146b6adf37f2d9925a6b2
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07378423B2

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