Acetonitrile → HCID 86704211, Verbindung

HRID 624030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624030
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Cl[CH2:10][C:11]([NH:13][C:14]1[N:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][N:15]=1)=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].CC#N>C(Cl)Cl>[CH3:21][O:20][C:18]1[C:17]([O:22][CH3:23])=[CH:16][N:15]=[C:14]([NH:13][C:11](=[O:12])[CH2:10][N:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]2)[N:19]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 68283152HCID 68283152, Verbindung

Produkt 1

HCID 86704211HCID 86704211, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A flask was charged with 4-nitro-1H-pyrazole (A) (317 mg, 2.8 mmol), 2-chloro-N-(4,5-dimethoxypyrimidin-2-yl)acetamide (2.26 mmol), Cs2CO3 (1.0 g, 3.09 mmol) and MeCN (9.0 mL). The resulting reaction mixture was stirred at reflux (80° C.) for 1 h, then allowed to reach rt. The mixture was diluted with DCM, filtered, the filter cake was washed with DCM. The filtercake was redisolved in DCM and water, the org. layer was separated and the aq. layer was extracted with DCM (2×). The combined org. layers were washed with brine, dried (MgSO4), filtered and concentrated to yield N-(4,5-dimethoxypyrimidin-2-yl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide as a crude which was used in the next step without further purification. LC-MS conditions B: tR=0.46 min, [M+H]+=309.10.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customto reach rt
  3. filtrationfiltered
  4. washthe filter cake was washed with DCM
  5. customlayer was separated
  6. extractionthe aq. layer was extracted with DCM (2×)
  7. washlayers were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4a9573990c0843c6bdfd8fc2e11877eb
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303023B2

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