Lawesson's reagent → (S)-1-(3-(4-dimethylaminothieno[3,2-d]pyrimidin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanethione

HRID 1666648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666648
[CH3:1][N:2]([CH3:32])[C:3]1[C:4]2[S:31][CH:30]=[CH:29][C:5]=2[N:6]=[C:7]([NH:9][C@H:10]2[CH2:14][CH2:13][N:12]([C:15](=O)[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:11]2)[N:8]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:32])[C:3]1[C:4]2[S:31][CH:30]=[CH:29][C:5]=2[N:6]=[C:7]([NH:9][C@H:10]2[CH2:14][CH2:13][N:12]([C:15](=[S:42])[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:11]2)[N:8]=1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 57970137(S)-1-(3-(4-dimethylaminothieno[3,2-d]pyrimidin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone

Produkt 1

HCID 57970083(S)-1-(3-(4-dimethylaminothieno[3,2-d]pyrimidin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanethioneAusbeute 26,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of (S)-1-(3-(4-dimethylaminothieno[3,2-d]pyrimidin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone (0.10 g), Lawesson's reagent (0.087 g), and toluene (10 mL) was heated at 110° C. for 5 h with stirring. After left stand for cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform/methanol=50:1) to obtain light yellow solid (S)-1-(3-(4-dimethylaminothieno[3,2-d]pyrimidin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanethione (0.027 g).

Aufarbeitung

  1. waitAfter left stand
  2. temperaturefor cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (silica gel, chloroform/methanol=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-8e0aa53b57d749cb83b38dc49998109e
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044068B2

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