2,6-Lutidine → HCID 136146825、化合物

HRID 1719078ノート

反応式

HRID 1719078 の反応式
[CH2:1]([C:3]1[N:4]=[C:5]([CH2:38][CH2:39][CH3:40])[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[OH:21])[CH3:2].[N:41]1C(C)=CC=CC=1C.FC(F)(F)S(O[Si](C(C)C)(C(C)C)C(C)C)(=O)=O.[C:67]([O:70]CC)(=[O:69])C>ClCCl>[CH2:1]([C:3]1[N:4]=[C:5]([CH2:38][CH2:39][CH3:40])[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[NH:41][C:67](=[O:69])[O:70][N:37]=3)=[CH:28][CH:29]=2)[C:7](=[O:22])[C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[OH:21])[CH3:2]

参加物

6

反応物 4

HCID 79372,6-LutidineHCID 8857Ethyl AcetateHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 594694034'-{[4-ethyl-5-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile

生成物 1

HCID 136146825HCID 136146825、化合物収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 4′-{[4-ethyl-5-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile (1.5 g) and 2,6-lutidine (0.98 mL) in dichloromethane (10 mL) was added triisopropylsilyl trifluoromethanesulfonate (1.5 mL) at 0° C. After stirring for 2 hr, the reaction mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was dissolved in dimethyl sulfoxide (5 mL), and then hydroxylamine hydrochloride (1.7 g) and sodium hydrogen carbonate (2.5 g) were added. The mixture was stirred overnight at 90° C. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was dissolved in tetrahydrofuran (5 mL), and N,N′-carbonyldiimidazole (0.6 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.6 mL) were added. After stirring for 30 min, the reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.3 g, 77%).

後処理

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in dimethyl sulfoxide (5 mL)
  5. additionhydroxylamine hydrochloride (1.7 g) and sodium hydrogen carbonate (2.5 g) were added
  6. stirringThe mixture was stirred overnight at 90° C
  7. temperatureAfter cooling
  8. additionthe reaction mixture was diluted with ethyl acetate
  9. washwashed with water
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. dissolutionThe residue was dissolved in tetrahydrofuran (5 mL)
  13. additionN,N′-carbonyldiimidazole (0.6 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.6 mL) were added
  14. stirringAfter stirring for 30 min
  15. additionthe reaction mixture was diluted with ethyl acetate
  16. washwashed with 1 M hydrochloric acid
  17. dry with materialdried over sodium sulfate
  18. concentrationconcentrated
  19. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9fbeade576064a9598cc484d7d3044e8
出典データセット
uspto-grants-2010_09
特許番号
US07803940B2

反応ノート

読み込み中…