Bromine → 2-[(5-Bromopyrimidin-4-yl)methyl]isoindoline-1,3-dione

HRID 2092031노트

반응식

HRID 2092031 반응식
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[N:6][CH:7]=1.BrBr.[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K]>C(O)(=O)C.C(OCC)(=O)C.O.[OH-].[Na+]>[Br:1][C:2]1[C:3]([CH2:8][N:15]2[C:11](=[O:21])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14]2=[O:16])=[N:4][CH:5]=[N:6][CH:7]=1

참가 물질

8

반응물 3

HCID 24408BromineHCID 124618635-Bromo-4-methylpyrimidineHCID 24194345Phthalimide potassium salt

생성물 1

HCID 595745872-[(5-Bromopyrimidin-4-yl)methyl]isoindoline-1,3-dione수율 88.3%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

5-Bromo-4-methylpyrimidine (2.90 g, 16.8 mmol) in acetic acid (40 mL) was stirred with bromine (3.18 g, 20.2 mmol) at 80° C. for 40 minutes. After completion of the reaction, the reaction solution was cooled, diluted with ethyl acetate and neutralized with water and 1 M aqueous sodium hydroxide, and the organic layer was separated, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1). The resulting product (3.69 g) was dissolved in 60 mL of dimethylformamide and heated with potassium phthalimide (2.84 g, 15.3 mmol) at 80° C. for 1 hour with stirring. After completion of the reaction, the reaction solution was mixed with water and extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform) to give the desired product (4.3 g, 80% yield).

후처리

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)
  7. dissolutionThe resulting product (3.69 g) was dissolved in 60 mL of dimethylformamide
  8. customAfter completion of the reaction
  9. extractionextracted with chloroform
  10. dry with materialthe extract was dried over anhydrous magnesium sulfate
  11. customevaporated under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography (chloroform)

출처 및 근거

ORD 기록
ord-8a893667f25944d6b8d7ec4c8e521e35
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440666B2

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