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

HRID 1666648Notes

Reaction equation

[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

Participants

Conditions

Temperature: 110 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-8e0aa53b57d749cb83b38dc49998109e
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044068B2

Reaction notes

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