Sodium hydride → HCID 86704207, Verbindung

HRID 624012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624012
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][OH:11])[CH:8]=1)([O-:3])=[O:2].[H-].[Na+].Cl[C:15]1[N:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[N:16]=1>C1COCC1>[CH3:24][O:23][C:17]1[CH:18]=[C:19]([O:21][CH3:22])[N:20]=[C:15]([O:11][CH2:10][CH2:9][N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[N:6]2)[N:16]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1620552-(4-Nitro-1H-pyrazol-1-yl)ethan-1-olHCID 51523232-Chloro-4,6-dimethoxypyrimidine

Produkt 1

HCID 86704207HCID 86704207, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cooled solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanol (1.90 g, 12.02 mmol) in THF (60 mL), NaH (673 mg, 16.82 mmol, 60%) was added and the solution was stirred for 5 min at 0° C., then the ice bath was removed and the reaction mixture was stirred at rt for 30 min, before 2-chloro-4,6-dimethoxypyrimidine (2.31 g, 13.22 mmol) was added. After 40 min at rt, the reaction mixture was quenched with water and the org. solvent was removed in vacuo. The aq. layer was extracted with DCM (1×), then acidified with 1 N HCl-solution to pH 2, and extracted with DCM (2×). The combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent removed under reduced pressure. Purification by crystallization (DCM-hept-mixture) yielded 4,6-dimethoxy-2-(2-(4-nitro-1H-pyrazol-1-yl)ethoxy)pyrimidine as a beige solid. LC-MS conditions A: tR=0.88 min, [M+H]+=295.98.

Aufarbeitung

  1. additionwas added
  2. customthe ice bath was removed
  3. additionwas added
  4. waitAfter 40 min at rt
  5. customthe reaction mixture was quenched with water
  6. customsolvent was removed in vacuo
  7. extractionThe aq. layer was extracted with DCM (1×)
  8. extractionextracted with DCM (2×)
  9. washlayers were washed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure
  13. customPurification
  14. customby crystallization (DCM-hept-mixture)

Quellen und Nachweise

ORD-Eintrag
ord-832a44f153694ebd9fc1c6d75eccc172
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303023B2

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