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22nd March 2018 @ 16:25

Method:

2-chloro-6-(2-hydrazinyl(benzylidene))pyrazine) (40.0 mg, 0.172 mmol, 1.0 equiv.) was dissolved in dry dichloromethane (15 mL) forming a yellow solution. Diacetoxyiodobenzene (PIDA) (55.4 mg, 0.172 mmol, 1.0 equiv.) was then added and the solution was stirred at room temperature under nitrogen for approximately 16 hours. After this time, the reaction mixture was exposed to air and analysed by TLC (1:1 EtOAc: PET ether) showing a clear product peak. The reaction mixture was quenched by the addition of a saturated aqueous solution of sodium hydrogen carbonate (~15 mL). Aqueous layers were separated and then extracted with DCM (2 x 15 mL). The organic layers were combined and washed with brine (1 x 20 mL), dried with MgSO4, filtered and evaporated in vacuo, yielding the crude product as a fine yellow powder (22.5 mg, 56.5%). The crude product was characterised using 1H NMR and IR. The product was purified using a silica column and the pure product (yellow solid) was obtained in vacuo (19.7 mg, 49.5%). The product was characterised by 1H NMR, 13C NMR, DEPT 90 + 135, GC-MS and IR.


Attached Files
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1H NMR Unsubstituted triazolopyrazine formation.pdf