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

HRID 627691ノート

反応式

HRID 627691 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-9b58c4912d044adcbc9583346485c84d
出典データセット
uspto-grants-2016_04
特許番号
US09309263B2

反応ノート

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