Methanol → 6-[(1-Oxopentyl)amino]-2-butyl-5-methylimidazo[4,5-b]pyridine

HRID 36112

Reaktionsgleichung

[NH2:1][C:2]1[C:7]([N+]([O-])=O)=[C:6]([CH3:11])[C:5]([N+:12]([O-])=O)=[CH:4][N:3]=1.[CH2:15]1[CH2:19]O[CH2:17][CH2:16]1.[C:20]([OH:26])(=O)[CH2:21][CH2:22][CH2:23][CH3:24].[NH4+:27].[OH-].[CH3:29]O>O.[Ni]>[O:26]=[C:20]([NH:27][C:16]1[CH:17]=[C:4]2[NH:3][C:2]([CH2:7][CH2:6][CH2:11][CH3:29])=[N:1][C:5]2=[N:12][C:15]=1[CH3:19])[CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 2-amino-3,5-dinitro-4-methylpyridine (5.2 g, 26 mmol), THF (100 mL), methanol (1300 mL) and Raney-nickel (3 mL of a 1:1 suspension in H2O) was stirred under H2 (1 atm.) for 5 h. The mixture was quickly filtered into a flask containing 3 ml of conc. HCl and the solvent was removed in vacuo at r.t. To the resulting crude 2,3,5-triamino-6-methylpyridine HCl complex was added valeric acid (8.68 mL, 80 mmol) and polyphosphoric acid (100 mL) and this mixture was heated to 80° C. for 7 h. The warmed mixture was poured into stirred ice-H2O (500 mL) and this mixture was cooled and neutralized (to pH 3) by the addition of conc. NH4OH. Extraction with CH2Cl2 (5×50 mL), drying (Na2SO4), concentration and purification (SiO2, 5% MeOH/EtOAc) gave the title compound as a solid.

Aufarbeitung

filtrationThe mixture was quickly filtered into a flask
additioncontaining 3 ml of conc. HCl
customthe solvent was removed in vacuo at r.t
additionThe warmed mixture was poured
temperaturethis mixture was cooled
extractionExtraction with CH2Cl2 (5×50 mL)
customdrying
concentration(Na2SO4), concentration and purification (SiO2, 5% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-6de85dba48e842268fe764ab41bd33f6
Quelldatensatz: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05412097

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