Pyridine → HCID 68650701, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-amino-6-(3-hydroxymethylphenyl)-N-methylpyrazine-2-carboxylate (75 mg, 0.3 mmol) was taken into THF (2 mL) followed by addition of pyridine (120 uL, 1.5 mmol) and the solution was cooled to 0° C. Thionyl chloride (42 uL, 0.6 mmol) was added to the mixture by syringe followed by warming to room temperature. The mixture was then stirred for two hours and partitioned with ethyl acetate and 1 M aqueous hydrochloric acid. The organic layer was washed with water (1x) then brine and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated followed by silica gel flash chromatography using ethyl acetate:hexanes (1:1) as eluent. The pure fractions were combined and concentrated then dried in vacuo to give methyl 3-amino-6-(3-chloromethylphenyl)-N-methylpyrazine-2-carboxylate (30 mg, 37% yield) as a yellow solid: MS (EI) for C13H13N3O2Cl: 278, 280 (MH+).

Provenance & Evidence