Dimethylformamide → HCID 59853046, 화합물

HRID 1670208노트

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HRID 1670208 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[OH:19].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([O:19][C:11]2[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=2[F:9])[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 775312,4-Dichloropyrimidine

생성물 1

HCID 59853046HCID 59853046, 화합물수율 53%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

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온도
100 °C

실험 절차

A mixture of 2,4-dichloropyrimidine (Aldrich, 0.74 g, 5.0 mmol), 2-fluoro-4-nitrophenol (Avacado, 0.79 g, 5.0 mmol), K2CO3 (0.76 g, 5.5 mmol), and DMF (50 mL) was heated at 100° C. for 2 h. The mixture was cooled and diluted with saturated NaHCO3 solution (100 mL) and extracted with EtOAc. The EtOAc extract was washed with brine, dried (MgSO4) and concentrated in vacuo to give a mixture of the 2-phenoxy- and 4-phenoxypyrimidine regioisomers as a yellow solid. The regioisomers were separated by flash chromatography using 10-40% EtOAc in hexanes as the eluent to give the title compound (0.71 g, 53%) as a white solid. 1H NMR (DMSO-d6) δ 8.76 (dd, 1H, J=6.0, 1.6 Hz), 8.43 (dt, 1H, J=9.8, 2.2 Hz), 8.23 (dd, 1H, J=8.8, 1.6 Hz), 7.80 (dt, 1H, J=9.8, 2.2 Hz), 7.48 (dd, 1H, J=6.0, 2.2 Hz).

후처리

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give
  8. customThe regioisomers were separated by flash chromatography

출처 및 근거

ORD 기록
ord-5c89bf943a3d4f539efc3ccc0d96e223
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989477B2

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