Dimethylformamide → 3-cyclopropyl-6-ethyl-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1889443ノート

反応式

HRID 1889443 の反応式
[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[CH:11]=[C:12]([CH2:14][CH3:15])[S:13][C:7]=3[NH:6][C:5]2=[O:16])[CH2:3][CH2:2]1.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[N:35]=[C:34](C(Cl)(Cl)Cl)[O:33][N:32]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-:41].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[CH:11]=[C:12]([CH2:14][CH3:15])[S:13][C:7]=3[N:6]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]4[NH:35][C:34](=[O:41])[O:33][N:32]=4)=[CH:21][CH:20]=3)[C:5]2=[O:16])[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 15290996HCID 15290996、化合物HCID 593516793-cyclopropyl-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

生成物 1

HCID 1360524063-cyclopropyl-6-ethyl-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione収率 58.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-cyclopropyl-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.25 g), 3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole (0.55 g), potassium carbonate (0.18 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography and dissolved in tetrahydrofuran (5 mL) and methanol (5 mL). 1N Aqueous sodium hydroxide solution (5 mL) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was adjusted to pH 4 with water and 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.3 g, 56%).

後処理

  1. washwashed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography
  5. dissolutiondissolved in tetrahydrofuran (5 mL)
  6. addition1N Aqueous sodium hydroxide solution (5 mL) was added
  7. stirringthe mixture was stirred at room temperature for 2 hr
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe obtained ethyl acetate layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-49db611744dd4b1e87052c1beecaf06e
出典データセット
uspto-grants-2013_08
特許番号
US08501750B2

反応ノート

読み込み中…