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

HRID 1666648노트

반응식

HRID 1666648 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 57970083(S)-1-(3-(4-dimethylaminothieno[3,2-d]pyrimidin-2-ylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanethione수율 26.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8e0aa53b57d749cb83b38dc49998109e
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044068B2

반응 노트

불러오는 중…