5-Fluorouracil → 5-Fluoro-1-hexadecanoylpyrimidine-2,4(1H,3H)-dione

HRID 371916

Reaktionsgleichung

Reaktionsgleichung von HRID 371916
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:10](Cl)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[O:27]1CCOCC1>N1C=CC=CC=1>[C:10]([N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])(=[O:27])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

5

Edukt 3

HCID 33855-FluorouracilHCID 209931-ChlorohexadecaneHCID 312751,4-Dioxane

Produkt 1

HCID 203522105-Fluoro-1-hexadecanoylpyrimidine-2,4(1H,3H)-dioneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2.6 g of 5-fluorouracil was suspended in 20 ml of absolute dioxane and 10 ml of absolute pyridine, and 15 g of palmityl chloride was added to the suspension followed by heating at 80° C for 1 hour while stirring. After completion of the reaction, the solvent was removed under reduced pressure (25 mm Hg), and the residual solid was washed with hot hexane (50° C). Any insoluble matter in the hot hexane was recrystallized from benzene to obtain 4.0 g of 1-N-palmitoyl-5-fluorouracil in a yield of 54%. Melting Point: 98° C.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe solvent was removed under reduced pressure (25 mm Hg)
  3. washthe residual solid was washed with hot hexane (50° C)
  4. customAny insoluble matter in the hot hexane was recrystallized from benzene

Quellen und Nachweise

ORD-Eintrag
ord-36ced0fe39214ae9805af2a1e9c49364
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04088646

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