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7th November 2014 @ 07:02

Resynthesis of TM 34-4

Resynthesis of 2-chloro-6-hydrazinylpyrazine (TM 34-3).

Reaction performed by William Talbot, Sebastian Schwartz and Hugh Russell.


First step in the synthesis (below) to prepare four chloroarylpyrazine cores.


2,6-dichloropyrazine (21 g, 141 mmol) was dissolved in 100 mL EtOH and hydrazine hydrate (13.5 mL, 270 mmol) was added. The mixture was stirred under reflux for 7 h.  At this time tlc (DCM) showed the presence of a new material (Rf =0.21).  The cooled, crude mixture was allowed to stand overnight.

The solvent was then removed from the crude mixture in vacuo, giving an orange mixture of oil and solid to which EtOAc (200mL) and  water (150mL) was added. The aqueous layer was removed and washed with EtOAc (3x 100mL). The combined organic layers were concentrated in vacuo to produce an orange crystalline solid. 

11.84 g of crude was produced.



ClC1=CN=CC(Cl)=N1 to



InChI=1S/C4H2Cl2N2/c5-3-1-7-2-4(6)8-3/h1-2H to


Attached Files
osm-step-1 risk assess.pdf
Re: Synthesis of 2-chloro-6-hydrazinylpyrazine (SGS 1-1) by Matthew Todd
15th November 2014 @ 23:09
Hi Hugh. So what do we reckon the solid is - the right thing? Does it TLC like this compound should - like previous preps of it? Do you plan on doing any characterisation on it, like a melting point?
Re: Matthew Todd by Hugh Russell
19th November 2014 @ 06:28
Hi Matt,
Unfortunately we do not have access to melting point apparatus here at school. Hopefully we should be able to get it NMR tested at Sydney Uni. We haven’t been able to find anyone else’s TLCs of the product (if there are, could someone please share them?) but ours looks fairly messy and impure.

Edit: We have now found melting apparatus at the school and should be able to characterise it.