Methyl iodide → N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)-N-methylacetamide

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Reaction Steps

According to Scheme 9 Step 1: To a solution of N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide (70 mg, 0.17 mmol) in THF (3 mL) was added portionwise at 0° C. sodium hydride (55%) 11 mg, 0.26 mmol). The suspension was stirred 10 minutes at room temperature. Then, methyl iodide (87 μl, 1.40 mmol) was added dropwise and the reaction mixture was stirred at room temperature under nitrogen atmosphere overnight. The mixture was diluted with 100 mL of a saturated solution of ammonium chloride and the aqueous layer was extracted twice with 100 mL of DCM. The organic layers were combined to be successively dried over MgSO2, filtered and concentrated under reduced pressure to afford a brown solid. The crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 10 g SiO2) using CH2Cl2/MeOH 99/1 as eluant to afford N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)-N-methylacetamide (54 mg, 75%) as a white solid.

Provenance & Evidence