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Sodium hydride → 1-Cyclopropyl-6,7-difluoro-8-methoxy-1H-quinazoline-2,4-dione

HRID 729406
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HRID 729406 반응식
[CH:1]1([NH:4][C:5]([NH:7][C:8](=[O:20])[C:9]2[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([O:17][CH3:18])[C:10]=2F)=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].[NH4+].[Cl-]>O1CCCC1.CN(C)C=O>[CH:1]1([N:4]2[C:10]3[C:9](=[CH:14][C:13]([F:15])=[C:12]([F:16])[C:11]=3[O:17][CH3:18])[C:8](=[O:20])[NH:7][C:5]2=[O:6])[CH2:3][CH2:2]1
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참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 112776651-Cyclopropyl-3-(3-methoxy-2,4,5-trifluorobenzoyl)urea

생성물 1

HCID 112656421-Cyclopropyl-6,7-difluoro-8-methoxy-1H-quinazoline-2,4-dione

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028
Tetrahydrofuran
용매

실험 절차

A solution of 1-cyclopropyl-3-(3-methoxy-2,4,5-trifluorobenzoyl)urea (Example 27b, 0.94 g, 3.26 mmol) in tetrahydrofuran (20 mL) and N,N-dimethylformamide (5 mL) is treated with sodium hydride (0.275 g, 6.8 mmol, 60% in mineral oil dispersion) and heated at reflux for 16 hours. The mixture is cooled, treated with saturated NH4Cl and extracted with dichloromethane. The organic layer is then washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Flash column chromatography (1:3 ethyl acetate/hexanes) afforded the title compound. MS (EI, M+1) m/z 269.

후처리

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. temperatureThe mixture is cooled
  4. extractionextracted with dichloromethane
  5. washThe organic layer is then washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d521ddb5a41e4020997d70d9bfe50003
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07582627B2

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