p-Toluenesulfonic acid → 2-(2-(Methylthio)pyrimidin-4-yl)acetonitrile

HRID 629485ノート

反応式

HRID 629485 の反応式
C(OC(=O)[CH:7]([C:16]#[N:17])[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=1)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][S:14][C:10]1[N:9]=[C:8]([CH2:7][C:16]#[N:17])[CH:13]=[CH:12][N:11]=1

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 51034226Cyano-(2-methylthio-pyrimidin-4-yl)-acetic acid tert-butyl ester

生成物 1

HCID 671997982-(2-(Methylthio)pyrimidin-4-yl)acetonitrile

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of Intermediate cyano-(2-methylthio-pyrimidin-4-yl)-acetic acid tert-butyl ester (5.3 g, 20 mmol) in anhydrous toluene (100 mL) was added p-toluenesulfonic acid (800 mg). The mixture was heated to reflux for 8 h, cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution and brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (3:1 hexanes/ethyl acetate eluant) to afford the title compound: 1H NMR 400 MHz (CDCl3) δ 8.56 (d, 1H), 7.12 (d, 1H), 3.84 (s, 2H), 2.57 (s, 3H); MS m/z: 166.0 (M+1).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 1N aqueous sodium hydroxide solution and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (3:1 hexanes/ethyl acetate eluant)

出典と根拠

ORDレコード
ord-ba8208fd542546c9954abedf052cb8d4
出典データセット
uspto-grants-2016_04
特許番号
US09314464B2

反応ノート

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