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22nd January 2014 @ 03:27

Using the following method, 8.34 g of methyl pyrazine-2-carboxylate (Preparation of OSM-S-147) was synthesised with a percentage yield of 60 %.

Experimental Procedure
Pyrazine-2-carboxylic acid (12.5 g, 101 mmol) was added to methanol (100 mL) and the solution cooled to 0 oC. Concentrated sulfuric acid (0.625 mL) was then added dropwise with stirring, ensuring the temperature did not exceed 5 oC. The mixture was refluxed at 85 oC for 22 h then cooled to room temperature (TCL plate). The methanol was then removed in vacuo and dichloromethane (50 mL) and water (25 mL) were added. Saturated sodium bicarbonate solution (~150 mL) was added until a pH of approximately 7.5 was reached. The organic layer was isolated and the remaining water layer extracted once more with dichoromethane (25 mL). The bright yellow organic layers were combined and dried over anhydrous magnesium sulfate. The crude product was isolated under vacuum. Purification by column chromatography was carried out with an eluent system of ethyl acetate and petroleum benzine (1:1) to yield pure white crystalline methyl pyrazine-2-carboxylate (yield: 8.34 g, 60.4 mmol, 59.9 %).

Hazard Assessment:

Synthesis of methyl pyrazine-2-carboxylate.docx

InChI:

InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)

to

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

TLC plate:

1H NMR:

1H NMR IT 1-1 pure DMSO.pdf
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Attached Files
Synthesis of methyl pyrazine-2-carboxylate.docx
Synthesis of methyl pyrazine-2-carboxylate.png
TCL IT 1-1 after reflux 22 h.png
1H NMR IT 1-1 pure DMSO.pdf
Comments
Re: Synthesis of methyl pyrazine-2-carboxylate (IT 1-1) by Alice Williamson
22nd January 2014 @ 03:45
HIRAC approved. Discussed the use of an ice bath when adding sulfuric acid to modify the procedure.
Re: Synthesis of methyl pyrazine-2-carboxylate (IT 1-1) by OSDD Malaria
27th January 2014 @ 09:37
Inga - great. How long did you reflux for? And are you following a procedure for this reaction - if so could you share the link? And do you know if this exact molecule has been made before? If so can you somehow link to a site/resource/paper with it in? The procedure and compound data may be in the same paper, but sometimes are not. Mat