Dimethyl Sulfoxide → 1-(4-Nitrophenyl)pyrimidine-2,4-dione

HRID 2106763

Reaktionsgleichung

Reaktionsgleichung von HRID 2106763
[H-].[Na+].CS(C)=O.[NH:7]1[CH:12]=[CH:11][C:10](=[O:13])[NH:9][C:8]1=[O:14].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>O>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([N:7]2[CH:12]=[CH:11][C:10](=[O:13])[NH:9][C:8]2=[O:14])=[CH:17][CH:18]=1)([O-:24])=[O:23]

Komponenten

6

Edukt 4

HCID 679Dimethyl Sulfoxide2×HCID 1174UracilHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydride

Produkt 1

HCID 112763381-(4-Nitrophenyl)pyrimidine-2,4-dioneAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirred solution of 42.8 parts of sodium hydride dispersion 50% in 200 parts of dimethyl sulfoxide was added dropwise slowly a solution of 50 parts of 2,4(1H,3H)-pyrimidinedione in 800 parts of dimethyl sulfoxide while the temperature was kept constant (20° C.) by cooling in an ice/water bath. 62.9 Parts of 1-fluoro-4-nitrobenzene were added and the whole was stirred overnight at 50° C. After cooling, the reaction mixture was poured into 2500 parts of water. The whole was washed with dichloromethane. The aqueous phase was brought to pH 5-6. The product was filtered off and stirred in 2-propanone. The product was filtered off and dried in vacuo at 60° C., yielding 60 parts (57.6%) of 1-(4-nitrophenyl)-2,4(1H,3H)-pyrimidinedione; mp.>300° C. (int. 23).

Aufarbeitung

  1. custom(20° C.)
  2. temperatureby cooling in an ice/water bath
  3. temperatureAfter cooling
  4. washThe whole was washed with dichloromethane
  5. filtrationThe product was filtered off
  6. stirringstirred in 2-propanone
  7. filtrationThe product was filtered off
  8. customdried in vacuo at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-c2fcd2a5cac34cc68e16028d5d86afc3
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04931444

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