Cesium carbonate → HCID 67502133, 화합물

HRID 1187779

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HRID 1187779 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:26]=[N:27][C:28]([NH2:31])=[N:29][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[N:17][C:18]([NH:31][C:28]3[N:29]=[CH:30][C:25]([Cl:24])=[CH:26][N:27]=3)=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 794792-Pyrimidinamine, 5-chloro-HCID 86664597(S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 67502133HCID 67502133, 화합물수율 35%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

In a pressure tube, (S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.94 g), 5-chloropyrimidin-2-amine (357 mg) and cesium carbonate (1.35 g) were combined with dioxane (5 ml) to give a yellow suspension. The mixture was degassed by bubbling through argon for several minutes. Xantphos (96 mg) and tris(dibenzylideneacetone)dipalladium chloroform complex (86 mg) were then added and the tube was sealed. The reaction mixture was stirred at 100° C. overnight. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography (SiO2; gradient: 0% to 70% EtOAc in hexane) to afford (S)-4-{2-[6-(5-chloro-pyrimidin-2-ylamino)-pyridin-3-yl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (417 mg, 35%) as a yellow solid. MS (ISP): 436.3 ([{37Cl}M+H]+), 434.4 ([{35Cl}M+H]+), 380.3 ([{37Cl}M+H—C4H8]+), 378.3 ([{35Cl}M+H—C4H8]+).

후처리

  1. customto give a yellow suspension
  2. customThe mixture was degassed
  3. customby bubbling through argon for several minutes
  4. additionXantphos (96 mg) and tris(dibenzylideneacetone)dipalladium chloroform complex (86 mg) were then added
  5. customthe tube was sealed
  6. temperatureThe reaction mixture was then cooled to room temperature
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (SiO2; gradient: 0% to 70% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-f273365661e146b49088d1877efa9cdc
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673950B2

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