Pyridine → 2-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine

HRID 1034592노트

반응식

HRID 1034592 반응식
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.N1C=CC=CC=1.[Br:22]Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]([Br:22])=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 24408BromineHCID 156743865-(4-Methoxyphenyl)pyrazin-2-amine

생성물 1

HCID 715237102-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine수율 70%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

To a solution of 2-amino-5-(4-mcthoxyphenyl)pyrazinc 16a (0.35 g, 1.7 mmol) and pyridine (0.20 mL, 2.6 mmol) in chloroform (20 mL), bromine (Br2) (0.13 mL, 2.6 mmol) was added dropwise in chloroform (3 mL) at −10° C. After 6 h stirring at room temperature, the reaction mixture was washed with water, the organic layer dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography using dichloromethane-EtOAc (90:10 v/v) as eluent, to obtain 0.33 g of 17a as an brown solid (mp 166-170° C., 70% yield). 1H-NMR (CDCl3): 3.83 (s, 3H), 5.04 (br s, 2H), 6.92-6.96 (m, 2H), 7.76-7.80 (m, 2H), 8.31 (s, 1H). GC-MS (EI): m/z 279,281 (M1, 100).

후처리

  1. washthe reaction mixture was washed with water
  2. dry with materialthe organic layer dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-fa0d033ad63b4d21ba822ff8ba9e0442
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546147B2

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