Hydrochloric Acid → 2-(3,5-Difluorophenyl)-5-pentylpyrimidine

HRID 2267979노트

반응식

HRID 2267979 반응식
[Mg].[F:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([F:9])[CH:8]=1.Cl[C:12]1[N:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][N:13]=1.Cl>O1CCCC1.Cl[Ni]Cl>[F:2][C:3]1[CH:4]=[C:5]([C:12]2[N:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:16][N:17]=2)[CH:6]=[C:7]([F:9])[CH:8]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1363131-Bromo-3,5-difluorobenzeneHCID 5462224MagnesiumHCID 167565262-Chloro-5-pentylpyrimidine

생성물 1

HCID 183482702-(3,5-Difluorophenyl)-5-pentylpyrimidine수율 15.4%

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

Grignard reagent was prepared from dried magnesium and 49.0 g (254 mmol) of 3,5-difluorobromobenzene in 200 ml of tetrahydrofuran (THF), 1 g of NiCl2 (dppp) was added thereto, 36.0 g (195 mmol) of the 2-chloro-5-pentylpyrimidine described above was added dropwise thereto, and the product was heated to reflux for 2 hours. The reaction solution was cooled down, and added into 200 ml of 1N-hydrochloric acid. The product was extracted with ether, and the extract was washed with saturated aqueous solution of sodium bicarbonate and water in turn, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure. The residue was purified by silica gel column chromatography (eluent: heptane/toluene=1/1) to obtain 8.0 g (30 mmol) of 2-(3,5-difluorophenyl)-5-pentylpyrimidine. Yield of this product was 15%.

후처리

  1. additionwas added
  2. additionabove was added dropwise
  3. temperaturethe product was heated
  4. temperatureto reflux for 2 hours
  5. temperatureThe reaction solution was cooled down
  6. extractionThe product was extracted with ether
  7. washthe extract was washed with saturated aqueous solution of sodium bicarbonate and water in turn
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under a reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: heptane/toluene=1/1)

출처 및 근거

ORD 기록
ord-2ff8042a9d594a9287bcec7bd91a2a0a
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326065B1

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