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A search in Scifinder was conducted for reaction conditions for the below generic schemes. The purpose of this was to find conditions to conduct a model experiment to create the ether linkage on 2,6-dichloropyrazine before attempting the same reaction with the triazolopyrazine, which we only have in very low yields.
A search for each scheme was performed using the reaction structure search and ticking the ‘substructure’ box. The reactions were filtered by:
- Yields of 70-100%
- Journals in English
- Must have an available experimental procedure.
Promising experiments/conditions for pyrazines:
Yield of 94%
Yield of 83%
Promising experiments/conditions for pyridines:
There are several options for the alcohol here, each with different yields.
90% where Ar = 2-MeO-C6H4 and R = H
92% where Ar = 4-MeO-C6H4 and R = H
96% where Ar = C6H5 and R = Me
75% where Ar = 4-CF3-C6H4 and R = H
93% where Ar = 4-Cl-C6H4 and R = H
Yield of 95%
I will start by trying the reaction from reference 4, but using 2,6-dichloropyrazine instead of the 2-chloropyradine as it is closer to the triazolopyrazine. I will also use phenethyl alcohol (HO(CH2)2C6H5) as this is closest to the ether I will eventually use to link to the triazolopyrazine. I will also attempt this reaction using 2,6-dichloropyrazine and the 4-MeO-C6H4 alcohol listed above as a comparison. Next week I will try the reactions from references 1 and 2 as their reaction times are longer than what I can achieve this afternoon.