Ethyl orthoformate → Ethyl acetate methanol ammonium hydroxide

HRID 397493Notes

Reaction equation

HRID 397493 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[N:6][CH:5]=1.[CH:13](OCC)(OCC)[O:14]CC>C(O)=O>[CH3:13][CH2:1][O:2][C:3]([CH3:4])=[O:12].[CH3:13][OH:14].[NH4+:6].[OH-:2].[CH3:1][O:2][C:3]([C:4]1[CH:5]=[N:6][C:7]2[N:11]=[CH:13][NH:10][C:8]=2[CH:9]=1)=[O:12]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 9920476Methyl 5,6-diaminopyridine-3-carboxylate

Product 2

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 71433321Methyl 1h-imidazo[4,5-b]pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl-5,6-diaminonicotinate (461 mg, 2.76 mmol), formic acid (250 μL) and triethyl orthoformate (7.5 mL) was heated to 100° C. for 2 h. The mixture was then concentrated to an oily solid. Silica gel chromatography (8:1:1 EtOAc-MeOH—NH4OH) afforded the title compound as a cream-colored solid: Rf (8:1:1 EtOAc-MeOH—NH4OH)=0.22; 1H NMR (400 MHz, DMSO-d6): δ8.94 (d, J=2.0 Hz, 1H), 8.64 (s, 1H), 8.50 (d, J=2.0 Hz, 1H), 3.91 (s, 3H).

Workup

  1. concentrationThe mixture was then concentrated to an oily solid

Sources & evidence

ORD record
ord-6c3abf7ed18846c09fa666755f45f827
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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