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Phosphorus oxychloride → 1-(4-bromo-phenyl)-6-chloro-3-cyclopropyl-1H-pyrimidine-2,4-dione

HRID 2224153
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HRID 2224153 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=O)[CH2:12][C:11](=[O:15])[N:10]([CH:16]3[CH2:18][CH2:17]3)[C:9]2=[O:19])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:22])=O.BrC1C=CC(N2C(=O)C=C(Cl)N(C3CC3)C2=O)=CC=1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([Cl:22])=[CH:12][C:11](=[O:15])[N:10]([CH:16]3[CH2:18][CH2:17]3)[C:9]2=[O:19])=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 597170143-(4-Bromo-phenyl)-6-chloro-1-cyclopropyl-1h-pyrimidine-2,4-dioneHCID 597170511-(4-Bromo-phenyl)-3-cyclopropyl-pyrimidine-2,4,6-trione

생성물 1

HCID 597170931-(4-bromo-phenyl)-6-chloro-3-cyclopropyl-1H-pyrimidine-2,4-dione수율 93%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 1-(4-bromo-phenyl)-3-cyclopropyl-pyrimidine-2,4,6-trione 32 (11.8 g) obtained in Step 2 was added water (1.31 ml) and phosphorus oxychloride (17.0 ml) was added dropwise with stirring at room temperature. After the completion of the dropwise addition, the mixture was stirred at 110° C. for 3 hrs. After allowing to cool to room temperature, the reaction mixture was added to ice water by small portions and the mixture was stirred. The mixture was stirred at room temperature and extracted with chloroform. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=2:1→chloroform:acetone=30:1) to give a 1:1.4 mixture (11.6 g, yield 93%) of 1-(4-bromo-phenyl)-6-chloro-3-cyclopropyl-1H-pyrimidine-2,4-dione 33 and 3-(4-bromo-phenyl)-6-chloro-1-cyclopropyl-1H-pyrimidine-2,4-dione 34 as a pale-yellow foamy oil.

후처리

  1. additionwas added dropwise
  2. additionAfter the completion of the dropwise addition
  3. stirringthe mixture was stirred at 110° C. for 3 hrs
  4. temperatureto cool to room temperature
  5. stirringthe mixture was stirred
  6. stirringThe mixture was stirred at room temperature
  7. extractionextracted with chloroform
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAnhydrous magnesium sulfate was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe residue was purified by column chromatography (hexane:ethyl acetate=2:1→chloroform:acetone=30:1)

출처 및 근거

ORD 기록
ord-50f63f0a0de44a0b91d9af5223cacf06
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07378423B2

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