Trimethylsilyldiazomethane → Methyl 2-(5-amino-4-methyl-2-pyridinyl)acetate

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 2-(4-methyl-5-pivalamidopyridin-2-yl)acetate (0.200 g, 0.653 mmol) was refluxed in hydrochloric acid 6N (10 ml) overnight. The reaction was concentrated then re-dissolved in MeOH (10 ml) and cooled to 0° C. then added TMS-diazomethane (0.653 ml, 1.305 mmol). When no SM was observed by TLC, the reaction was quenched with glacial acetic acid and concentrated. The residue was taken up with ethyl acetate and washed with NaHCO3. The organic layer was dried over NaSO4, filtered and evaporated to dryness. The residue was purified by chromatography using 40 g ISCO Redisep column and 5% MeOH/DCM solvent system to yield title compound.

Provenance & Evidence