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

HRID 1831577Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

(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].

Workup

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

Sources & evidence

ORD record: ord-da150a454b334525bf43a110e76c0844
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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