Dimethylformamide → 3-butyl-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 1889440ノート

反応式

HRID 1889440 の反応式
[CH2:1]([N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[C:13]([CH2:15][CH3:16])[S:14][C:8]=2[NH:7][C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]2[N:36]=[C:35](C(Cl)(Cl)Cl)[O:34][N:33]=2)=[CH:22][CH:21]=1.CN(C)C=[O:44].[H-].[Na+]>C(OCC)(=O)C>[CH2:1]([N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[C:13]([CH2:15][CH3:16])[S:14][C:8]=2[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[NH:36][C:35](=[O:44])[O:34][N:33]=3)=[CH:22][CH:21]=2)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 15290996HCID 15290996、化合物HCID 593517803-butyl-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

生成物 1

HCID 1360523983-butyl-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%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a mixture of 3-butyl-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (1 g), 3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole (1.89 g) and N,N-dimethylformamide (50 mL) was added sodium hydride (0.17 g), and the mixture was stirred at 50° C. for 1 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. To the obtained residue was added 1N aqueous sodium hydroxide solution (50 mL), and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was adjusted to pH 4 with 1N hydrochloric acid, 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, and the obtained solid was recrystallized from tetrahydrofuran-diisopropylether to give the title compound as colorless crystals (1.13 g, 58%).

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. additionTo the obtained residue was added 1N aqueous sodium hydroxide solution (50 mL)
  5. stirringthe mixture was stirred at 60° C. for 1 hr
  6. extractionextracted with ethyl acetate
  7. washThe obtained ethyl acetate layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography
  11. customthe obtained solid was recrystallized from tetrahydrofuran-diisopropylether

出典と根拠

ORDレコード
ord-cc66c0710ab84a14936625eace6d92b8
出典データセット
uspto-grants-2013_08
特許番号
US08501750B2

反応ノート

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