Acetic Acid → 3-Methoxy-5-methylpyrazine-2-carboxamide

HRID 1978138Notes

Reaction equation

[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].C[O-].[Na+].[C:11]([OH:14])(=O)C.[CH3:15][C:16]([CH:18]=O)=O>CO>[CH3:11][O:14][C:6]1[C:2]([C:3]([NH2:5])=[O:4])=[N:1][CH:15]=[C:16]([CH3:18])[N:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Under argon, 6 g (60.5 mmol) of 2-amino-2cyanoacetamide was initially charged in 67 g of methanol. 1.67 g (9.3 mmol) of sodium methoxide solution (30%) was added and the mixture was stirred for at 20° C. 2 hours. After nuetralization with 0.558 g (9.3 mmol) of acetic acid, 11.55 g (64.1 mmol) of methylglyoxal solution (40%) was added. The mixture was stirred at 20° C. for 2 hours and then at 50° C. for 2 hours. The solvent was distilled off and the 3-methoxy-5-methylpyrazine-2-carboxamide was purified by column chromatography (eluent: ethyl acetate/methanol 4:1). This gave 5 g of 3-methoxy-5-methylpyrazine-2-carboxamide. The yield was 50 percent. Other data concerning the title product was: 1H-NMR (DMSO-d6, 400 MHz) 5: 8.10 (s, 1H);

Workup

custom2 hours
stirringThe mixture was stirred at 20° C. for 2 hours
distillationThe solvent was distilled off
customthe 3-methoxy-5-methylpyrazine-2-carboxamide was purified by column chromatography (eluent: ethyl acetate/methanol 4:1)

Sources & evidence

ORD record: ord-01778542408b4981b1ea789c689eed47
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235905B1

Reaction notes

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