2-[4-(4-Acetoxybenzoyl)benzylthio]-3,5-dimethylthieno[2,3-d]pyrimidin-4(3H)-one → 3,5-dimethyl-2-[4-(4-hydroxybenzoyl)benzylthio]thieno[2,3-d]pyrimidin-4(3H)-one

HRID 1291340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291340
C([O:4][C:5]1[CH:32]=[CH:31][C:8]([C:9]([C:11]2[CH:30]=[CH:29][C:14]([CH2:15][S:16][C:17]3[N:18]([CH3:28])[C:19](=[O:27])[C:20]4[C:25]([CH3:26])=[CH:24][S:23][C:21]=4[N:22]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].O>O1CCCC1>[CH3:28][N:18]1[C:19](=[O:27])[C:20]2[C:25]([CH3:26])=[CH:24][S:23][C:21]=2[N:22]=[C:17]1[S:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([C:9](=[O:10])[C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:32][CH:31]=2)=[CH:30][CH:29]=1

Komponenten

4

Edukt 2

HCID 189192392-[4-(4-Acetoxybenzoyl)benzylthio]-3,5-dimethylthieno[2,3-d]pyrimidin-4(3H)-oneHCID 23719242Sodium hydroxide--water (1/1/1)

Produkt 1

HCID 189188093,5-dimethyl-2-[4-(4-hydroxybenzoyl)benzylthio]thieno[2,3-d]pyrimidin-4(3H)-oneAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-[4-(4-acetoxybenzoyl)benzylthio]-3,5-dimethylthieno [2,3-d]pyrimidin-4(3H)-one (1.40 g) and 1N-sodium hydroxide/water (6.7 ml) in tetrahydrofuran (20 ml) was stirred at room temperature for 10 minutes. This reaction mixture was concentrated and the residue was dissolved in water and acidified with 1N-HCl. The resulting precipitate was extracted with ethyl acetate, washed with water, dried, and concentrated. The residue was recrystallized from methanol-ethyl acetate to provide the title compound as colorless solid (775 mg).

Aufarbeitung

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionThe resulting precipitate was extracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from methanol-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ad1d5983f0db4483a923af585f431b90
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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