Pyridine → 3-Benzyl-5-bromopyrazin-2-amine

HRID 1034591노트

반응식

HRID 1034591 반응식
[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[Br-:21].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:5]([Br:21])=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 27625483-Benzylpyrazin-2-amineHCID 23500184Tetra-n-butylammonium tribromide

생성물 1

HCID 27625493-Benzyl-5-bromopyrazin-2-amine수율 89%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 3-benzyl-2-aminopyrazine 12 (1.38 g, 7.40 mmol) in chloroform (40 mL), pyridine (1.80 mL, 22.00 mmol) and tetrabutylamoniumtribromide TBATB (3.57 g, 7.40 mmol) were added at room temperature. After 1 h the reaction mixture was washed with 20% aqueous solution of NaCl, the organic layer was then dried over Na2SO4, filtered and the solvent removed under reduced pressure. The crude was purified by flash chromatography (EtOAc-dichloromethane, 80:20) to get 1.75 g (89% yield) of the title compound 13 as a pale brown solid and subsequent recrystallization (n-exane/diethyl ether) gave colorless crystals suitable for crystallographic studies. 1H-NMR (CDCl3): 3.97 (s, 2H), 4.74 (br s, 2H), 7.10-7.24 (m, 5H), 7.89 (s, 1H). MS (ESI): m/z 265 (M+H). The crystallography of compound 13 is shown in FIG. 3, demonstrating its purity.

후처리

  1. washAfter 1 h the reaction mixture was washed with 20% aqueous solution of NaCl
  2. dry with materialthe organic layer was then dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe crude was purified by flash chromatography (EtOAc-dichloromethane, 80:20)
  6. customto get

출처 및 근거

ORD 기록
ord-95410e8f9f22433098c094debba439ff
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546147B2

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