Toluene → 5-Chloropyrido[3,4-b]pyrazin-2(1H)-one

HRID 930443

Reaktionsgleichung

Reaktionsgleichung von HRID 930443
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[C:10](OCC)(=O)[CH:11]=[O:12].C1(C)C=CC=CC=1>C(O)C>[Cl:1][C:2]1[C:7]2[N:8]=[CH:10][C:11](=[O:12])[NH:9][C:6]=2[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 2857362-Chloropyridine-3,4-diamine

Produkt 1

HCID 867157425-Chloropyrido[3,4-b]pyrazin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A suspension 2-chloropyridine-3,4-diamine (2.5 g, 17.41 mmol) and a 50% solution of ethyl glyoxalate in toluene (3.45 mL, 17.41 mmol) in ethanol (34.8 mL) was stirred at reflux for 24 hours. The solution was cooled to −20° C. for 16 hours, and the resulting precipitate was collected by vacuum filtration and rinsed with ethanol. The crude product was purified via reverse-phase HPLC, eluting with 5-50% acetonitrile/0.1% trifluoroacetic acid in water/0.1% TFA, to afford the title compound (570 mg, 3.14 mmol). MS m/z=182 (M+H).

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. filtrationthe resulting precipitate was collected by vacuum filtration
  3. washrinsed with ethanol
  4. customThe crude product was purified via reverse-phase HPLC
  5. washeluting with 5-50% acetonitrile/0.1% trifluoroacetic acid in water/0.1% TFA

Quellen und Nachweise

ORD-Eintrag
ord-720f5dcaf5bc45448e7957b61be0d748
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296734B2

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