Dimethylformamide → Methyl 5,6-dichloro-3-methylpyrazine-2-carboxylate

HRID 627691노트

반응식

HRID 627691 반응식
[Cl:1][C:2]1[N:3]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:5]([CH3:9])=[N+:6]([O-])[CH:7]=1.P(Cl)(Cl)([Cl:16])=O.CN(C=O)C>C1(C)C=CC=CC=1>[Cl:16][C:7]1[N:6]=[C:5]([CH3:9])[C:4]([C:10]([O:12][CH3:13])=[O:11])=[N:3][C:2]=1[Cl:1]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 867281445-Chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide

생성물 1

HCID 86728145Methyl 5,6-dichloro-3-methylpyrazine-2-carboxylate수율 68%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 5-chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide (8.83 g, 43.6 mmol) in toluene (100 mL) at 0° C. was added phosphorus oxychloride (10 ml, 109 mmol) and DMF (1 ml, 12.91 mmol). The reaction mixture was stirred at room temperature for 1 h, and then was heated to 85° C. fort 8 h. The mixture was cooled to RT and concentrated. The residue was diluted with EtOAc and washed with saturated NaHCO3 solution. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude mixture was purified with ISCO (0% to 10% EtOAc/Hexanes) to afford the desired methyl 5,6-dichloro-3-methylpyrazine-2-carboxylate (6.51 g, 68% yield). 1H NMR (300 MHz, CDCl3) δ ppm 4.00 (3H, s), 2.83 (3H, s)

후처리

  1. temperaturewas heated to 85° C.
  2. waitfort 8 h
  3. temperatureThe mixture was cooled to RT
  4. concentrationconcentrated
  5. additionThe residue was diluted with EtOAc
  6. washwashed with saturated NaHCO3 solution
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude mixture was purified with ISCO (0% to 10% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-9b58c4912d044adcbc9583346485c84d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309263B2

반응 노트

불러오는 중…