Cesium carbonate → 4-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine

HRID 1619444ノート

反応式

HRID 1619444 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[C:13]([CH3:14])=[C:12]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)[N:11]=[CH:10][N:9]=1.[CH3:28][C:29]1([CH3:42])[O:34][CH2:33][CH:32]([C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)[CH2:31][O:30]1>CN(C=O)C>[CH3:28][C:29]1([CH3:42])[O:30][CH2:31][CH:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41][C:8]3[C:13]([CH3:14])=[C:12]([O:15][CH:16]4[CH2:21][CH2:20][N:19]([C:22]5[N:27]=[CH:26][CH:25]=[CH:24][N:23]=5)[CH2:18][CH2:17]4)[N:11]=[CH:10][N:9]=3)=[CH:37][CH:36]=2)[CH2:33][O:34]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 675102564-(2,2-Dimethyl-1,3-dioxan-5-yl)phenolHCID 866651634-Chloro-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine

生成物 1

HCID 675115354-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine収率 68.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

Cesium carbonate (2.97 mg, 0.00914 moles) was added to a solution 4-chloro-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine (1.39 gm, 0.00457 moles) and 4-(2,2-dimethyl-1,3-dioxan-5-yl)phenol (950 mg, 0.00457 moles) in dry DMF (10 ml) and the reaction mixture was stirred at 60° C. for 12 hours. Then reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product so obtained was purified by column chromatography (silica gel) using 22% ethyl acetate in hexane as eluent to obtain 1.5 gm product as white solid.

後処理

  1. customThen reaction mixture
  2. additionwas poured into ice cold water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas successively washed with water & brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product so obtained
  9. customwas purified by column chromatography (silica gel)

出典と根拠

ORDレコード
ord-8a17741720f0431eb858ecd613c322b0
出典データセット
uspto-grants-2014_07
特許番号
US08772302B2

反応ノート

読み込み中…