Tetrahydrofuran → 2-Chloro-4-(4-fluorobenzyloxy)pyrimidine

HRID 15064

반응식

HRID 15064 반응식
C([Li])CCC.O1CCCC1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=1.[Cl:20][C:21]1[N:26]=[C:25](Cl)[CH:24]=[CH:23][N:22]=1>O>[Cl:20][C:21]1[N:26]=[C:25]([O:17][CH2:16][C:15]2[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=2)[CH:24]=[CH:23][N:22]=1

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 680224-Fluorobenzylic alcoholHCID 775312,4-DichloropyrimidineHCID 178418339Butyllithium

생성물 1

HCID 860707302-Chloro-4-(4-fluorobenzyloxy)pyrimidine수율 68%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

n-Butyl lithium (2.6 M n-hexane solution, 10.1 mL) was added to tetrahydrofuran solution (12 mL) of 4-fluorobenzyl alcohol (3.08 mL) at −78° C., and stirred at the same temperature for 30 minutes. This reaction liquid was gradually added to tetrahydrofuran suspension (24 mL) of 2,4-dichloropyrimidine (4.0 g) and stirred at room temperature for 2 hours. After addition of water, the reaction liquid was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was crystallized from mixed solvent of chloroform and hexane to provide the title compound (4.36 g, 68%).

후처리

  1. customThis reaction liquid
  2. stirringstirred at room temperature for 2 hours
  3. customthe reaction liquid
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentrating the solvent under reduced pressure
  8. customthe residue was crystallized
  9. additionfrom mixed solvent of chloroform and hexane

출처 및 근거

ORD 기록
ord-ab4bf3d2c4494cc991525056ab6da85b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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