Hydrogen Bromide → Ethyl 2-bromo-3-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl]propionate

HRID 1419004

반응식

HRID 1419004 반응식
[CH2:1]([C:3]1[N:4]([CH2:11][CH2:12][O:13][C:14]2[CH:20]=[CH:19][C:17](N)=[CH:16][CH:15]=2)[C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[N:8]=1)[CH3:2].[BrH:21].N([O-])=O.[Na+].[C:26]([O:30][CH2:31][CH3:32])(=[O:29])[CH:27]=[CH2:28]>CC(C)=O.O.[Cu]I>[Br:21][CH:27]([CH2:28][C:17]1[CH:19]=[CH:20][C:14]([O:13][CH2:12][CH2:11][N:4]2[C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[N:8]=[C:3]2[CH2:1][CH3:2])=[CH:15][CH:16]=1)[C:26]([O:30][CH2:31][CH3:32])=[O:29]

참가 물질

8

반응물 4

HCID 260Hydrogen BromideHCID 8821Ethyl AcrylateHCID 219601564-[2-[2-Ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]anilineHCID 23668193Sodium Nitrite

생성물 1

HCID 21960196Ethyl 2-bromo-3-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl]propionate수율 55%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]aniline (2.80 g, 10.26 mmol) (obtained from preparation 22) in acetone (10 ml) was added aqueous HBr (47%, 1 ml) and stirred for 10 min. at 0° C. To the above reaction mixture a solution of NaNO2 (850 mg, 12.30 mmol) in water (1.7 ml) was added slowly dropwise at 0° C. and stirring was continued further for 30 min at the same temperature. To this reaction mixture, ethyl acrylate (6.77 ml, 62.0 mmol) was added and allowed to warm to 30° C. Catalytic amount of copper (I) iodide (20 mg) was added in one portion and the reaction mixture was stirred further for 1 h at 30° C. Acetone was removed under reduced pressure and the resultant residue was extracted with EtOAc (3×10 ml). The combined EtOAc layers were washed with dilute NH3 solution, water, followed by brine; dried over anhydrous Na2SO4 and concentrated to afford the crude compound which was purified by flash chromatography using 40% EtOAc/petroleum ether as eluent to yield the title compound (2.47 g, 55%).

후처리

  1. stirringstirring
  2. waitwas continued further for 30 min at the same temperature
  3. temperatureto warm to 30° C
  4. stirringthe reaction mixture was stirred further for 1 h at 30° C
  5. customAcetone was removed under reduced pressure
  6. extractionthe resultant residue was extracted with EtOAc (3×10 ml)
  7. washThe combined EtOAc layers were washed with dilute NH3 solution, water
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated
  10. customto afford the crude compound which
  11. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-f3e1eb63d5114f4e8792a629b3650349
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05885997

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