Phosphorus oxychloride → 3,6-Dichloropyrido[2,3-b]pyrazine

HRID 2199906노트

반응식

HRID 2199906 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][C:8](=O)[NH:9][C:10]=2[N:11]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:8]1[N:9]=[C:10]2[N:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=[N:6][CH:7]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 866975626-Chloropyrido[2,3-b]pyrazin-3(4H)-one

생성물 1

HCID 866975633,6-Dichloropyrido[2,3-b]pyrazine수율 90%

실험 절차

6-chloropyrido[3,2-b]pyrazin-3(4H)-one (E-27) (9 g, 49.8 mmol) was dissolved in POCl3 (100 mL) and the resulting mixture was stirred at reflux for 3 h. The reaction was complete based on TLC analysis. The mixture was cooled to RT and concentrated in vacuo to remove POCl3. The residue was poured into ice water (150 mL) and extracted with DCM (3×100 mL). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the desired product 3,6-dichloropyrido[2,3-b]pyrazine (E-28) (9 g, 90% yield) as a solid. ESI-MS m/z: 199.97 [M+H]+.

후처리

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated in vacuo
  3. customto remove POCl3
  4. additionThe residue was poured into ice water (150 mL)
  5. extractionextracted with DCM (3×100 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-9599de175ee44bc5aa58c152b05d7b02
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359352B2

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