Methanethiol → 2'-Deoxy-2'-methylthiouridine

HRID 612839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612839
[CH:1]1[C:15](=[O:16])[N:14]=C2[N:3]([C@@H:4]3[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]3O2)[CH:2]=1.[CH3:17][SH:18].[CH3:19]N(C)C(N(C)C)=N>CN(C=O)C>[CH3:19][C@@H:5]1[C@H:6]([OH:11])[C@@H:7]([CH2:9][OH:10])[O:8][C@H:4]1[N:3]1[CH:2]=[CH:1][C:15](=[O:16])[NH:14][C:17]1=[S:18]

Komponenten

5

Edukt 3

HCID 878MethanethiolHCID 664601,1,3,3-TetramethylguanidineHCID 8061382,2'-Anhydrouridine

Produkt 1

HCID 1317202082'-Deoxy-2'-methylthiouridineAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,2'Anhydrouridine (15.5 g, 68.2 mmol) [Rao and Reese, J. Chem. Soc., Chem. Commun., 997], methanethiol (15.7 g, 327 mmol), 1,1,3,3-tetramethylguanidine (39.2 g, 341 mmol) and DMF (150 mL) were heated at 60° C. After 12 hours, the reaction mixture was cooled and concentrated under reduced pressure. The residual oil was purified by flash column chromatography on silica gel (300 g). Concentration of the appropriate fractions, which were eluted with CH2Cl2 --MeOH (9:1), and drying the residue under reduced pressure gave 2'-deoxy-2'-methylthiouridine as a pale yellow solid (14.11 g, 75.4%). Attempts to crystallize the solids from EtOH-hexanes [as reported by Imazawa et al., Chem. Pharm. Bull., 23, 604 (1975)] failed and the material turned into a hygroscopic foam.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residual oil was purified by flash column chromatography on silica gel (300 g)
  4. washConcentration of the appropriate fractions, which were eluted with CH2Cl2 --MeOH (9:1)
  5. customdrying the residue under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ac71f4fd6d2e4e7baac5a2f13f31273c
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06005087

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