Methyl pyruvate → (R)-8-chloro-4-(1-methoxymethylpropyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one

HRID 1831577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1831577
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C@@H:9]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[C:3]=1[NH2:15].[C:16](OC)(=[O:20])[C:17]([CH3:19])=O>CCCCO>[Cl:1][C:2]1[C:3]2[N:15]=[C:17]([CH3:19])[C:16](=[O:20])[N:8]([C@@H:9]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[C:4]=2[N:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 11748Methyl pyruvateHCID 69658257(R)-4-chloro-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine

Produkt 1

HCID 69658154(R)-8-chloro-4-(1-methoxymethylpropyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-oneAusbeute 133,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(R)-4-Chloro-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine (0.24 g, 1.04 mmol) was dissolved in n-BuOH, followed by methyl pyruvate (1.07 g, 10.4 mmol) and the reaction was heated at 60° C. for 5 h, before heating at reflux overnight. The reaction was concentrated in vacuo and purified by column chromatography (20% EtOAc/hex) to yield 0.39 g, 100% of (R)-8-chloro-4-(1-methoxymethylpropyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one: MS (AP) m/z 281.74 [(M+H)+, 100].

Aufarbeitung

  1. temperaturebefore heating
  2. temperatureat reflux overnight
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified by column chromatography (20% EtOAc/hex)

Quellen und Nachweise

ORD-Eintrag
ord-da150a454b334525bf43a110e76c0844
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067658B2

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