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 1889443노트

반응식

HRID 1889443 반응식
[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

참가 물질

6

반응물 4

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

생성물 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)-dione수율 58.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-49db611744dd4b1e87052c1beecaf06e
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501750B2

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