Vanillin → 5-(4-Formyl-2-methoxyphenoxy)pyrazine-2-carboxamide

Participants

Reaction Steps

Dissolve 5-chloropyrazine-2-carboxamide (Example 387, Part A) (0.374 g, 2.34 mmol) and vanillin (0.361 g, 2.34 mmol) in DMF (23.7 mL). Add K2CO3 (0.821 g, 8.94 mmol) and heat at 100° C. for 1.5 hours. Concentrate the reaction mixture. Take the solid up in water (50 mL) and extract with dichloromethane (3×100 mL). Dry the organic layer over Na2SO4, filter and concentrate to give the title compound (0.625 g, 96.4%): TOF MS ES+ 274.1 (M+H)+, HRMS calcd for C13H12N3O4 274.0828 (M+H)+, found 274.0829, time 0.55 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-95 over 19 min], tR=10.2 min, 98.1% purity.

Provenance & Evidence