2-Methyl-2-thiopseudourea sulfate → HCID 178503562, Verbindung

HRID 1366379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366379
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[F:11][CH:12]([C:17](OC)=[O:18])[C:13](OC)=[O:14].C[O-].[Na+]>CO>[F:11][C:12]1[C:13](=[O:14])[N:10]=[C:8]([S:7][CH3:6])[NH:9][C:17]=1[OH:18]

Komponenten

5

Edukt 3

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 2737111Dimethyl fluoromalonateHCID 10942334Sodium Methoxide

Produkt 1

HCID 178503562HCID 178503562, VerbindungAusbeute 135,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-methyl-2-thiopseudourea sulfate (41.7 g, 0.15 mol) and dimethyl fluoromalonate (45 g, 0.30 mol) in MeOH (600 mL) at 0° C. (ice bath) was added NaOMe (48.6 g, 0.90 mol) in portions. After the addition was complete, the ice bath was withdrawn and the reaction mixture was stirred at room temperature overnight. LCMS showed the formation of the desired pyrimidinone product. The reaction mixture was concentrated to near dryness under vacuum, diluted with water (50 mL), and acidified with 6N HCl (˜150 mL) to ˜pH 2 to precipitate the product. After filtration, the solid was washed with 1N HCl (2×10 mL) and dried under vacuum to afford 5-fluoro-6-hydroxy-2-methylthio-4(1H)-pyrimidinone (35.7 g, 68%) as a white solid. LCMS: (M+H)+: 177.3.

Aufarbeitung

  1. additionAfter the addition
  2. customthe ice bath was withdrawn
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with water (50 mL)
  5. customto precipitate the product
  6. filtrationAfter filtration
  7. washthe solid was washed with 1N HCl (2×10 mL)
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-acdfeb3181374c949c765d3e9f111f4e
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

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