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3rd February 2014 @ 00:33

13.12 g of impure methyl 4-oxy-2-pyrazine carboxylate was synthesised. Purification by column chromatography will be carried out after the next step of the reaction (see Synthesis of methyl 6-chloro-2-pyrazinecarboxylate (IT 3-1))

This synthesis is following the method used by Eduvie Omene: Repeat of Synthesis and purification of Methyl 4-oxy-2-pyrazinecarboxylate (EO 5-2) and Synthesis and purification of Methyl 4-oxy-2-pyrazinecarboxylate (EO 5-1), who seems to have been following the method used in this paper (DOI: 10.1021/jm201045m, see p. 7688).

Methyl-2-pryrazinecarboxylate (8.24 g, 59.7 mmol) was suspended in 1,2-dichloroethane (80 mL) and m-CPBA (24 g, 118 mmol, 85 % purity) was added. The reaction was stirred at 60 °C for 20 h. Starting material was still present (as seen by TLC) so more m-CPBA (1.352 g, 6.66mmol, 85 % purity) was added. After a further 5 h of heating, the temperature was raised to 70 °C because starting material was still present in the reaction mixture (seen by TLC). The mixture was cooled to RT after a total of 40 h heating and diluted with dichloromethane (250 mL). The precipitate was isolated by filtration and washed with dichloromethane (3 x 30 mL). The filtrates were dried over anhydrous potassium carbonate then concentrated in vacuo. The residue was suspended in hexane (40 mL) and the methyl 4-oxy-2-pyrazine carboxylate isolated by filtration. The crude product was washed with hexane (2 x 40 mL) to afford a pale yellow powder (13.12 g, 85.1 mmol, 143 %).

Hazard Assessment

Synthesis of methyl 4-oxy-2-pyrazine carboxylate.docx

Class 3 IT 2-1.png

InChI:

InChI=1S/C6H6N2O2/c1-10-6(9)5-4-7-2-3-8-5/h2-4H,1H3

to

InChI=1S/C6H6N2O3/c1-11-6(9)5-4-8(10)3-2-7-5/h2-4H,1H3

1H NMR

IT 2-1 workup today DMSO.pdf
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Attached Files
Synthesis of IT 2-1.png
Synthesis of methyl 4-oxy-2-pyrazine carboxylate.docx
Class 3 IT 2-1.png
IT 2-1 workup today DMSO.pdf
Comments
Re: Synthesis of methyl 4-oxy-2-pyrazine carboxylate (IT 2-1) by Alice Williamson
5th February 2014 @ 00:27
HIRAC seen and approved - awaiting upload of reaction label (class 3) to lab notebook. Discussed safe disposal and work up procedure and avoiding mixtures of peracids with certain solvents and caution on evaporation. Previous prep by Eduvie doesn't mention any exotherm on addition of mcpba - will proceed cautiously with ice bath to hand.