Cesium carbonate → HCID 67502133、化合物

HRID 1187779

反応式

HRID 1187779 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 67502133HCID 67502133、化合物収率 35%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-f273365661e146b49088d1877efa9cdc
出典データセット
uspto-grants-2014_03
特許番号
US08673950B2

関連ノート

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