Toluene → Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylate

HRID 50107

反応式

HRID 50107 の反応式
[NH2:1][C:2](=[C:10]([C:15](=O)[CH:16]([CH3:18])[CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.C1(C)C=CC=CC=1.[C:27]([N:29]([CH3:34])[S:30]([CH3:33])(=[O:32])=[O:31])#[N:28]>[Ti](Cl)(Cl)(Cl)Cl.O>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:15]([CH:16]([CH3:18])[CH3:17])[N:28]=[C:27]([N:29]([S:30]([CH3:33])(=[O:32])=[O:31])[CH3:34])[N:1]=2)=[CH:4][CH:5]=1

参加物

6

反応物 3

HCID 1140TolueneHCID 10219456N-cyano-N-methylmethanesulphonamideHCID 178500902HCID 178500902、化合物

生成物 1

HCID 9929821Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylate収率 80.3%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

10.0 g (37.7 mmol) of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate were introduced into 50 ml of toluene, together with 10.17 g (75.4 mmol) of N-cyano-N-methylmethanesulphonamide and the mixture was treated at room temperature with 3.61 g (18.9 mmol) of titanium tetrachloride. The reaction progressed exothermically. The red-orange-coloured suspension was heated to 110° C. and stirred for 4.5 h. It was then cooled to room temperature and treated with 30 ml of water. The organic phase was separated off and the aqueous phase was extracted with ethyl acetate (30 ml). The combined organic phases were washed with 30 ml of water and dried over magnesium sulphate. After filtering and concentrating the solution in a water-jet vacuum and drying in vacuo, 11.54 g of crude product were obtained in the form of a tacky oil.

後処理

  1. temperatureIt was then cooled to room temperature
  2. customThe organic phase was separated off
  3. extractionthe aqueous phase was extracted with ethyl acetate (30 ml)
  4. washThe combined organic phases were washed with 30 ml of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationAfter filtering
  7. concentrationconcentrating the solution in a water-jet vacuum
  8. customdrying in vacuo

出典と根拠

ORDレコード
ord-0efebf0306204be49d7b2753b8d39b9e
出典データセット
uspto-grants-2004_03
特許番号
US06710178B2

関連ノート

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