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

HRID 1291339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291339
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:12])=[CH:10][S:11][C:5]=2[N:4]=[C:3]1[SH:13].[OH-].[Na+].O.CN(C=O)C.[C:22]([O:25][C:26]1[CH:41]=[CH:40][C:29]([C:30]([C:32]2[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=2)=[O:31])=[CH:28][CH:27]=1)(=[O:24])[CH3:23]>C(O)C.O>[C:22]([O:25][C:26]1[CH:41]=[CH:40][C:29]([C:30]([C:32]2[CH:33]=[CH:34][C:35]([CH2:36][S:13][C:3]3[N:2]([CH3:1])[C:7](=[O:8])[C:6]4[C:9]([CH3:12])=[CH:10][S:11][C:5]=4[N:4]=3)=[CH:38][CH:39]=2)=[O:31])=[CH:28][CH:27]=1)(=[O:24])[CH3:23]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 189192074-(4-Acetoxybenzoyl)benzyl bromideHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178431876HCID 178431876, Verbindung

Produkt 1

HCID 189192392-[4-(4-Acetoxybenzoyl)benzylthio]-3,5-dimethylthieno[2,3-d]pyrimidin-4(3H)-oneAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3,5-dimethyl-2-mercaptothieno[2,3-d]pyrimidin-4(3H)-one (1.40 g) and 1N-sodium hydroxide/water (6.7 ml) in ethanol (13 ml)-DMF (25 ml) was added 4-(4-acetoxybenzoyl)benzyl bromide (2.68 g) and the mixture was stirred at room temperature at 60° C. for 1 hour. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated, and the residue was recrystallized from methanol to provide the title compound as colorless solid (887 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customthe residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-ef82eec2593b49b6b179ab00753fd34a
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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