Water → 2,6-Dioxo-5-[3-(3-trifluoromethyl-phenyl)-ureido]-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid

HRID 2262760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2262760
[NH2:1][C:2]1[C:10](=[O:11])[NH:9][C:8](=[O:12])[NH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:16]=[C:17]([N:21]=[C:22]=[O:23])[CH:18]=[CH:19][CH:20]=1.O>CS(C)=O>[O:12]=[C:8]1[NH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:1][C:22]([NH:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:24])[F:25])[CH:16]=2)=[O:23])[C:10](=[O:11])[NH:9]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 730185-Amino-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid

Produkt 1

HCID 111991292,6-Dioxo-5-[3-(3-trifluoromethyl-phenyl)-ureido]-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

5-Amino-orotic acid (0.86 g) was dissolved in DMSO (10 ml), treated with 3-trifluoromethylphenylisocyanate (0.9 ml) and after an hour with another 0.5 ml. The reaction was stirred for three days at room temperature. Water was added and the mixture was filtered and washed with water. The residue was slurried in water, treated with NaOH and worked through until basic. Filtration and acidification of the filtrate provided a precipitate, which was filtered, washed with water and dried. Recrystallisation from 96% EtOH provided 2,6-dioxo-5-[3-(3-trifluoromethyl-phenyl)-ureido]-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid (330 mg). Mp. >300° C.

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. washwashed with water
  3. additiontreated with NaOH
  4. filtrationFiltration and acidification of the filtrate
  5. customprovided a precipitate, which
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried
  9. customRecrystallisation from 96% EtOH

Quellen und Nachweise

ORD-Eintrag
ord-9bf8a49fe37047bdb27cf0f73cbbebec
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851492B2

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