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7th March 2014 @ 01:35
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: 1. 10.1021/np200386c Yield of 94% 2. 10.1021/jm061247v Yield of 83% Promising experiments/conditions for pyridines: 3. 10.1021/jo800866w There are several options for the alcohol here, each with different yields. 4. 10.1021/jo901707x 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   5. 10.1021/jo0602773 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.
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