Cesium carbonate → 5-(4-(6-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

HRID 1619441

反応式

HRID 1619441 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([O:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[O:25][N:24]=[C:23]([CH:26]([CH3:28])[CH3:27])[N:22]=3)[CH2:17][CH2:16]2)[C:9]=1[CH3:29].[CH3:30][C:31]1([CH3:44])[O:36][CH2:35][CH:34]([C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)[CH2:33][O:32]1>CN(C=O)C>[CH3:30][C:31]1([CH3:44])[O:32][CH2:33][CH:34]([C:37]2[CH:42]=[CH:41][C:40]([O:43][C:8]3[N:13]=[CH:12][N:11]=[C:10]([O:14][CH:15]4[CH2:20][CH2:19][N:18]([C:21]5[O:25][N:24]=[C:23]([CH:26]([CH3:28])[CH3:27])[N:22]=5)[CH2:17][CH2:16]4)[C:9]=3[CH3:29])=[CH:39][CH:38]=2)[CH2:35][O:36]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 675102564-(2,2-Dimethyl-1,3-dioxan-5-yl)phenolHCID 865973665-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

生成物 1

HCID 675159055-(4-(6-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole収率 44.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Cesium carbonate (755 mg, 0.002317 moles) was added to a solution of 5-(4-(6-chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole (1.2 gm, 0.003365 moles) and 4-(2,2-dimethyl-1,3-dioxan-5-yl)phenol (700 mg, 0.003365 moles) in dry DMF (10 ml) and the reaction mixture was stirred at 80° C. for 3 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 15% ethyl acetate in hexane as eluent to obtain 770 mg 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-8547c1dc5c5647e9843dc3f5e033f4f9
出典データセット
uspto-grants-2014_07
特許番号
US08772302B2

関連ノート

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