Methanol → Methyl 5-aminopyrimidine-2-carboxylate

Participants

Reaction Steps

A suspension of 5-aminopyrimidine-2-carboxylic acid (Goldenbridge Pharma, Inc.; 5.70 g, 41.0 mmol) in MeOH (120 mL) was cooled in an ice-water bath and treated dropwise with thionyl chloride (8.97 mL, 123 mmol). The resulting suspension was heated at reflux for 20 h and then concentrated to give a yellow solid. The solid was dissolved in saturated aqueous NaHCO3 (60 mL) and extracted into EtOAc using a Gregar Extractor. The extract was concentrated to give methyl 5-aminopyrimidine-2-carboxylate (4.26 g, 68% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.32 (s, 2H), 4.35 (br s, 2H), 4.02 (s, 3H).

Provenance & Evidence