5-Fluorouracil → HCID 10675385, Verbindung

HRID 2271262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2271262
[CH2:1]([Si:3]([C:8]#[C:9][C@:10]1([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:18][CH:13](OC(=O)C)[C@H:12]([O:19][C:20](=[O:22])[CH3:21])[C@@H:11]1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[F:40][C:41]1[C:42](=[O:48])[NH:43][C:44](=[O:47])[NH:45][CH:46]=1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(=O)([O-])O.[Na+]>ClCCCl>[C:20]([O:19][C@@H:12]1[C@H:31]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@:10]([C:9]#[C:8][Si:3]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:1][CH3:2])([CH2:11][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:18][C@H:13]1[N:45]1[CH:46]=[C:41]([F:40])[C:42](=[O:48])[NH:43][C:44]1=[O:47])(=[O:22])[CH3:21]

Komponenten

7

Edukt 5

HCID 33855-FluorouracilHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 12042250HCID 12042250, Verbindung

Produkt 1

HCID 10675385HCID 10675385, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Compound 6 (2.00 g, 3.62 mmol) was dissolved in 1,2-dichloroethane (60.0 ml), and 5-fluorouracil (0.71 g, 5.46 mmol) and N,O-bis(trimethylsilyl)acetamide (5.37 ml, 21.7 mmol) were added to the solution, followed by refluxing for one hour. After the reaction mixture was allowed to cool to room temperature, trimethylsilyl trifluoromethanesulfonate (0.85 ml, 4.70 mmol) was added thereto, followed by stirring overnight at 50° C. A saturated aqueous solution of sodium hydrogencarbonate was added to the mixture, and after stirring, the organic layer was dried over anhydrous magnesium sulfate. The residue was purified by means of silica gel column chromatography (silica gel 300 ml, eluent; n-hexane:ethyl acetate=3:1), to thereby yield a colorless viscous compound (Compound 31; 0.80 g, 1.28 mmol, 35.4%).

Aufarbeitung

  1. temperatureby refluxing for one hour
  2. stirringafter stirring
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe residue was purified by means of silica gel column chromatography (silica gel 300 ml, eluent; n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-664c38a4a34240d4878784decea552ea
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06333315B1

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