Dimethylformamide → HCID 59853046, 화합물

HRID 2237177노트

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HRID 2237177 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-b79b9064f63144c69a5c040e24cc2c83
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714138B2

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