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

HRID 1619446
ノート
印刷プレビュー

反応式

HRID 1619446 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].CS([O:11][CH2:12][C:13]1[N:14]=[C:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[CH2:20][CH2:19]2)[S:16][CH:17]=1)(=O)=O.[CH3:30][C:31]1([CH3:44])[O:36][CH2:35][CH:34]([C:37]2[CH:42]=[CH:41][C:40](O)=[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:11][CH2:12][C:13]3[N:14]=[C:15]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]5[N:29]=[CH:28][CH:27]=[CH:26][N:25]=5)[CH2:20][CH2:19]4)[S:16][CH:17]=3)=[CH:39][CH:38]=2)[CH2:35][O:36]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 675102564-(2,2-Dimethyl-1,3-dioxan-5-yl)phenolHCID 86665164(2-(1-(Pyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methyl methanesulfonate

生成物 1

HCID 675101514-((4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)methyl)-2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazole収率 114.8%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
60 °C

実験手順

Cesium carbonate (735 mg, 0.0022 moles) was added to a solution of (2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methyl methanesulfonate (490 gm, 0.00112 moles) and 4-(2,2-dimethyl-1,3-dioxan-5-yl)phenol (281 mg, 0.001384 moles) in DMF (10 ml) and the reaction mixture was stirred at 60° C. for 2 hours. Then the reaction mixture was then 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 600 mg product as white solid.

後処理

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

出典と根拠

ORDレコード
ord-d22b4ba1dc814256b05d29b7481e2133
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08772302B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート