Sodium Acetate → 3-Methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 567915

Reaktionsgleichung

Reaktionsgleichung von HRID 567915
[C:1]([O-])(=O)[CH3:2].[Na+].[CH3:6][N:7]1[C:12](=[O:13])[CH2:11][C:10](=[S:14])[N:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:8]1=[O:19]>O>[CH3:6][N:7]1[C:12](=[O:13])[C:11]2[CH:1]=[CH:2][S:14][C:10]=2[N:9]([CH2:15][CH:16]([CH3:17])[CH3:18])[C:8]1=[O:19]

Komponenten

4

Edukt 2

HCID 517045Sodium AcetateHCID 222580271-Isobutyl-3-methyl-6-thioxodihydropyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 52825273-Methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium acetate (38.9 g) was added to a stirred suspension of 3-methyl-1-(2-methylpropyl)-6-thioxo-pyrimidine-2,4(1H,3H)-dione (25.42 g) in water (11). After 5 hours, the mixture was filtered. Aqueous chloroacetaldehyde solution (50wt. %, 142 ml) was added to the filtrate and the mixture was stirred for 16 hours. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (3×500 ml). The combined organic extracts were washed with saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residual oil was purified by column chromatography over silica, eluting with isohexane: ether (1:1) to give the title compound (26.78 g) as a solid.

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. additionAqueous chloroacetaldehyde solution (50wt. %, 142 ml) was added to the filtrate
  3. extractionextracted with ethyl acetate (3×500 ml)
  4. washThe combined organic extracts were washed with saturated sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residual oil was purified by column chromatography over silica
  9. washeluting with isohexane: ether (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-390195654bf2433cbe8157016915c65e
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180635B2

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