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2-Fluoro-4-nitrophenol → 4-(2-Fluoro-4-nitrophenoxy)-6-(methylthio)thieno[3,2-d]pyrimidine

HRID 1261346
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HRID 1261346 반응식
Cl[C:2]1[C:3]2[S:10][C:9]([S:11][CH3:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[OH:23].C([O-])([O-])=O.[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1>[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[O:23][C:2]1[C:3]2[S:10][C:9]([S:11][CH3:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1
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5

반응물 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 594244514-Chloro-6-(methylthio)thieno[3,2-d]pyrimidine

생성물 1

HCID 594244784-(2-Fluoro-4-nitrophenoxy)-6-(methylthio)thieno[3,2-d]pyrimidine수율 88%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

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온도
130 °C

실험 절차

A mixture of 280 (210 mg, 0.97 mmol), 2-fluoro-4-nitrophenol (278 mg, 1.77 mmol) and K2CO3 (560 mg, 3.54 mmol) in Ph2O (10 mL) was heated at 130° C. 60 hours, cooled to room temperature and partitioned between EtOAc and water. Organic phase was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by flash column chromatography with a gradient elution (hexane to hexane/EtOAc, 1:1) to afford the title compound 281 (288 mg, 88% yield) as a yellowish solid. MS (m/z): 338.1(M+H) (found).

후처리

  1. temperature60 hours, cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. customOrganic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography with a gradient elution (hexane to hexane/EtOAc, 1:1)

출처 및 근거

ORD 기록
ord-368089bf9e954c4693d1e8196e3efc05
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08470850B2

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