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Triethylamine → 6-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1889343
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HRID 1889343 반응식
[NH2:1][C:2]1[S:3][C:4]([CH:11]2[CH2:13][CH2:12]2)=[CH:5][C:6]=1[C:7]([O:9]C)=O.Cl[C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:36]=1[CH2:43][NH2:44]>C(Cl)Cl>[CH:11]1([C:4]2[S:3][C:2]3[NH:1][C:15](=[O:17])[N:44]([CH2:43][C:36]4[CH:37]=[CH:38][C:39]([O:41][CH3:42])=[CH:40][C:35]=4[O:34][CH3:33])[C:7](=[O:9])[C:6]=3[CH:5]=2)[CH2:13][CH2:12]1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 5972502,4-DimethoxybenzylamineHCID 45089420Methyl 2-amino-5-cyclopropylthiophene-3-carboxylate

생성물 1

HCID 593517456-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione수율 100%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution (300 mL) of methyl 2-amino-5-cyclopropylthiophene-3-carboxylate (4.7 g) in methylene chloride were added triphosgene (3.06 g) and triethylamine (8.6 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added 1-(2,4-dimethoxyphenyl)methanamine (7.2 mL), and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (300 mL), sodium methoxide (6.4 g) was added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with 1N hydrochloric acid and chloroform. The chloroform layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (8.53 g, 100%).

후처리

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in methanol (300 mL)
  6. additionsodium methoxide (6.4 g) was added
  7. stirringthe mixture was stirred at 60° C. for 2 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. extractionthe obtained residue was extracted with 1N hydrochloric acid and chloroform
  10. washThe chloroform layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. filtrationThe precipitated solid was collected by filtration

출처 및 근거

ORD 기록
ord-df61078afda04cde92f4d5ffa24f2645
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501750B2

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