3-METHYLPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER Chemical Properties

Boiling point:

221.8±35.0 °C(Predicted)

Density 

1.169±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-0?+-.0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C7H8N2O2/c1-5-6(7(10)11-2)9-4-3-8-5/h3-4H,1-2H3

InChIKey

AUDOINDPGADJPY-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=CN=C1C

Safety Information

HS Code 

2933998090

3-METHYLPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Synthesis

3-Methylpyrazine-2-carboxylic acid (19.95 g, 144 mmol) was suspended in methanol (500 mL) in a 2L round bottom flask. The suspension was cooled in an ice-water bath, followed by slow dropwise addition of concentrated sulfuric acid (27.3 mL, 506 mmol) over 5 min. The reaction mixture was heated to 80 °C and maintained at this temperature for 5 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was dissolved in dichloromethane (750 mL). Excess acid was neutralized in small amounts with 5 M aqueous sodium hydroxide solution (200 mL). The aqueous layer was separated and extracted with dichloromethane (250 mL). All organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give methyl 3-methylpyrazine-2-carboxylate (16.15 g, 106 mmol, 73% yield). Mass spectral analysis showed m/z = 153 [M + H]+.

References

[1] Patent: US2014/213581, 2014, A1. Location in patent: Paragraph 0773; 0793
[2] Patent: WO2014/138484, 2014, A1. Location in patent: Page/Page column 147; 148
[3] Patent: WO2016/22724, 2016, A1. Location in patent: Page/Page column 292; 293
[4] Patent: WO2016/174073, 2016, A1. Location in patent: Page/Page column 44
[5] Patent: WO2010/130970, 2010, A1. Location in patent: Page/Page column 39-40

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