Ammonium Chloride → 1-(3-Benzylpyrido[2,3-b]pyrazin-6-yl]-3-ethylurea

HRID 1511821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511821
[Br-].[CH2:2]([Zn+])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[N:16]=[C:15]2[N:17]=[C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:20][C:14]2=[N:13][CH:12]=1.[Cl-].[NH4+]>C1COCC1.O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:2]([C:11]1[N:16]=[C:15]2[N:17]=[C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:20][C:14]2=[N:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

7

Edukt 3

HCID 25517Ammonium ChlorideHCID 588817911-(3-Chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylureaHCID 178419772HCID 178419772, Verbindung

Produkt 1

HCID 166673101-(3-Benzylpyrido[2,3-b]pyrazin-6-yl]-3-ethylurea

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2.4 ml of a 0.5 M solution of benzylzinc bromide (1.20 mmol) in THF and 24.7 mg of tetrakis(triphenylphosphine)palladium(0) (0.02 mmol) were initially charged in 1 ml of dioxane under nitrogen. Subsequently, 102.4 mg of 1-(3-chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea (0.41 mmol) and 1 ml of dioxane were added in portions. The mixture was then heated to 100° C. After 7 h, the reaction mixture was allowed to cool and then saturated ammonium chloride solution was added. The aqueous phase was extracted repeatedly with dichloromethane and the collected organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate and freed from the solvent under reduced pressure. Column chromatography purification on silica gel (dichloromethane/methanol eluent) afforded a yellow solid.

Aufarbeitung

  1. temperatureto cool
  2. extractionThe aqueous phase was extracted repeatedly with dichloromethane
  3. washthe collected organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customColumn chromatography purification on silica gel (dichloromethane/methanol eluent)
  6. customafforded a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-fcaa68700e01447b9ff11752a9251042
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217042B2

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