Dimethyl Sulfoxide → 2-ethoxy-6-methyl-3-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-5-phenylpyrimidin-4(3H)-one

HRID 1673624ノート

反応式

HRID 1673624 の反応式
[Cl-].O[NH3+:3].[C:4](=[O:7])([O-])[OH:5].[Na+].CS(C)=O.[CH2:13]([O:15][C:16]1[N:17]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[C:38]([C:43]#[N:44])=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:33][CH:32]=2)[C:18](=[O:29])[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:20]([CH3:22])[N:21]=1)[CH3:14]>O>[CH2:13]([O:15][C:16]1[N:17]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:43]3[NH:3][C:4](=[O:7])[O:5][N:44]=3)=[CH:35][CH:36]=2)[C:18](=[O:29])[C:19]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:20]([CH3:22])[N:21]=1)[CH3:14]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 574601004'-[(2-ethoxy-4-methyl-6-oxo-5-phenylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile

生成物 1

HCID 1360267552-ethoxy-6-methyl-3-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-5-phenylpyrimidin-4(3H)-one収率 24%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

A mixture of hydroxylammonium chloride (1.08 g), sodium hydrogen carbonate (1.53 g) and dimethyl sulfoxide (10 mL) was stirred at 40° C. for 30 min, 4′-[(2-ethoxy-4-methyl-6-oxo-5-phenylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile (0.77 g) was added, and the mixture was stirred at 90° C. for 5 hr. The mixture was allowed to cool to room temperature. Water was added to the reaction mixture, and the precipitate was collected by filtration. The obtained solid was dissolved in ethyl acetate. The solution was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was dissolved in tetrahydrofuran (5 mL), N,N′-carbonyldiimidazole (0.44 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.41 mL) were added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.21 g, 24%).

後処理

  1. stirringthe mixture was stirred at 90° C. for 5 hr
  2. temperatureto cool to room temperature
  3. filtrationthe precipitate was collected by filtration
  4. dissolutionThe obtained solid was dissolved in ethyl acetate
  5. washThe solution was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. dissolutionThe residue was dissolved in tetrahydrofuran (5 mL)
  9. additionN,N′-carbonyldiimidazole (0.44 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.41 mL) were added
  10. stirringthe mixture was stirred at room temperature for 30 min
  11. additionThe reaction mixture was diluted with ethyl acetate
  12. washwashed with 1 M hydrochloric acid
  13. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  14. customThe solvent was evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-5f19bc96c59c47f3b04e3534d3b454f6
出典データセット
uspto-grants-2011_08
特許番号
US07998968B2

反応ノート

読み込み中…