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27th September 2016 @ 19:24

(started on 9/25)

Link to last attempt: Synthesis of 2-Chloro-6-hydrazinylpyrazine (MRLS 1-1). Synthesizing more to re-attempt the synthesis of the triazolopyrazine core with fresh reagents (p-tsoh catalyst had a worrying NMR). 

 

first step of nemesis synthesis

compound

MW (g/mol)

mol (mmol) g           density (g/mL) volume (mL) equivalents
[2,6] dichloropyrazine 148.98 13.4 2     1
hydrazine hydrate 32.045 13.4 0.680   0.66 1
ethanol         20  
2-Chloro-6-hydrazinylpyrazine 144.56  13.4  1.937     1

 

[2,6]-Dichloropyrazine (2.01 g, 13.4 mmol) was stirred in ethanol (22 mL) and hydrazine hydrate (80% by volume, 0.80 mL). The mixture was refluxed at 80 ˚C  under Ar for ~24 hours. 

(9/26)

Solvent removed under reduced pressure. Crude yellow solid was produced. This solid was dissolved in 15 mL deionized water and 20 mL EtOAc. Aqueous layer extracted with 3x10mL EtOAc. All organic layers combined and washed with 10mL Brine. Solvent removed under reduced pressure to yield pale yellow product (0.761g, 5.24 mmol, 39% yield). Yield was so bad because I failed to realize that the hydrazine was in fact 83% hydrazine, so there was a lot of unreacted starting material left over once the hydrazine was used up. 

Attached Files
MRLS1-3clean.pdf
MRLS 1pdf.pdf