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Dimethyl Sulfoxide → 3-(2-{4-[2-(dimethylamino)ethoxy]phenyl}-2-oxoethyl)-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 1889524
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HRID 1889524 반응식
[Cl-].O[NH3+:3].[C:4](=[O:7])([O-])[OH:5].[Na+].CS(C)=O.[CH3:13][N:14]([CH3:55])[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:54])[CH2:25][N:26]2[C:31](=[O:32])[C:30]3[CH:33]=[C:34]([CH2:36][CH3:37])[S:35][C:29]=3[N:28]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([C:45]4[C:46]([C:51]#[N:52])=[CH:47][CH:48]=[CH:49][CH:50]=4)=[CH:41][CH:40]=3)[C:27]2=[O:53])=[CH:20][CH:19]=1>O.C(OCC)(=O)C>[CH3:55][N:14]([CH3:13])[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:54])[CH2:25][N:26]2[C:31](=[O:32])[C:30]3[CH:33]=[C:34]([CH2:36][CH3:37])[S:35][C:29]=3[N:28]([CH2:38][C:39]3[CH:40]=[CH:41][C:42]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=4[C:51]4[NH:3][C:4](=[O:7])[O:5][N:52]=4)=[CH:43][CH:44]=3)[C:27]2=[O:53])=[CH:20][CH:19]=1
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참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 593516204'-{[3-(2-{4-[2-(dimethylamino)ethoxy]phenyl}-2-oxoethyl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

생성물 1

HCID 136052308
3-(2-{4-[2-(dimethylamino)ethoxy]phenyl}-2-oxoethyl)-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
수율 57.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

A mixture of hydroxylammonium chloride (0.38 g), sodium hydrogencarbonate (0.58 g) and dimethyl sulfoxide (4 mL) was stirred at 50° C. for 30 min, 4′-{[3-(2-{4-[2-(dimethylamino)ethoxy]phenyl}-2-oxoethyl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (0.41 g) was added, and the mixture was stirred at 90° C. for 20 hr. After allowing to cool to room temperature, ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and 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 dissolved in tetrahydrofuran (4 mL). N,N′-Carbonyldiimidazole (0.13 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.12 mL) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed successively with 1N hydrochloric acid and 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 pale-yellow amorphous solid (0.26 g, 57%).

후처리

  1. stirringthe mixture was stirred at 90° C. for 20 hr
  2. temperatureto cool to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. dissolutiondissolved in tetrahydrofuran (4 mL)
  9. additionN,N′-Carbonyldiimidazole (0.13 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.12 mL) were added
  10. stirringthe mixture was stirred at room temperature for 2 hr
  11. additionThe reaction mixture was diluted with ethyl acetate
  12. washwashed successively with 1N hydrochloric acid and saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customThe solvent was evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-de1a4cef090546c1b1bb7ac30e1098b6
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501750B2

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