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

HRID 1034591ノート

反応式

HRID 1034591 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 27625493-Benzyl-5-bromopyrazin-2-amine収率 89%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-95410e8f9f22433098c094debba439ff
出典データセット
uspto-grants-2013_10
特許番号
US08546147B2

反応ノート

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