Ethyl orthoformate → 6-Bromo-8-chloro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1045727노트

반응식

HRID 1045727 반응식
[Br:1][C:2]1[N:3]=[C:4]([Cl:10])[C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH:11](OCC)(OCC)OCC>O>[Br:1][C:2]1[N:3]=[C:4]([Cl:10])[C:5]2[N:6]([CH:11]=[N:9][N:8]=2)[CH:7]=1

참가 물질

4

반응물 2

HCID 31214Ethyl orthoformateHCID 584469775-Bromo-3-chloro-2-hydrazinylpyrazine

생성물 1

HCID 584469856-Bromo-8-chloro[1,2,4]triazolo[4,3-a]pyrazine수율 87%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
130 °C

실험 절차

A 50 mL round bottom flask was charged with 5-bromo-3-chloro-2-hydrazinylpyrazine (1.24 g, 5.5 mmol) and triethyl orthoformate (20 mL). The resulting mixture was stirred at 130° C. for 2 h. Reaction progress was monitored by TLC (EtOAc/petroleum ether=1:2). Work-up: the reaction mixture was diluted with water and extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with 30% EtOAc in petroleum ether, to afford 1.12 g (87%) of the product as a red solid.

후처리

  1. customReaction progress
  2. extractionextracted with EtOAc (50 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was further purified by flash column chromatography on silica gel with 30% EtOAc in petroleum ether

출처 및 근거

ORD 기록
ord-f117d7fb853541d5abcca5fa78a22508
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569300B2

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