4-Fluoroaniline → 5-bromo-2-(4-fluorophenylamino)-3-methylpyrimidin-4(3H)-one

HRID 2241255노트

반응식

HRID 2241255 반응식
[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](Cl)=[N:6][CH:7]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>CCCCO.CCOC(C)=O>[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 97314-FluoroanilineHCID 516892Sodium BicarbonateHCID 673486115-bromo-2-chloro-3-methylpyrimidin-4(3H)-one

생성물 1

HCID 685151905-bromo-2-(4-fluorophenylamino)-3-methylpyrimidin-4(3H)-one수율 99%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of 5-bromo-2-chloro-3-methylpyrimidin-4(3H)-one (0.100 g, 0.448 mmol; prepared according to the procedure of Example 46, Step B), 4-fluorobenzenamine (0.056 ml, 0.582 mmol) and NaHCO3 (0.150 g, 1.79 mmol) in n-BuOH (3 mL) was stirred at 60° C. overnight. The reaction mixture was cooled to room temperature and then diluted with EtOAc. The EtOAc layer washed with H2O and saturated aqueous NaCl. The aqueous phase was re-extracted with EtOAc. The combined EtOAc layers were dried (Na2SO4), filtered and concentrated to yield the desired product (0.132 g, 99%) as a pale yellow solid that was used without further purification.

후처리

  1. customprepared
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washThe EtOAc layer washed with H2O and saturated aqueous NaCl
  4. extractionThe aqueous phase was re-extracted with EtOAc
  5. dry with materialThe combined EtOAc layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-14202cdaf4284259b330f52746160049
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723330B2

반응 노트

불러오는 중…