Sodium ethoxide → 5-Bromo-2-cyclopropylpyrimidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-cyclopropylpyrimidine was prepared by the method of Budesinsky, Z., Coll. Czech. Chem. Commun., 1949, 14, 223-235. Cyclopropanecarboximidamide hydrochloride (2.5 g, 20.7 mmol) was dissolved in EtOH (4 mL), freshly prepared 4.1M NaOEt in EtOH (4.8 mL) was added followed by mucobromic acid (2.7 g, 10.3 mmol). The mixture was heated to 56° C. for 30 minutes, more NaOEt in EtOH (4.1M, 3.2 mL) was added and the reaction was stirred at 56° C. for another 15 minutes and then at room temperature overnight. The solvent was evaporated off, aqueous HCl (2M, 10 mL) was added and the brown solid was filtered off. The aqueous layer was extracted three times with dichloromethane. The combined organic layers were dried and concentrated to give a brown oil that together with the solid gave crude intermediate 5-bromo-2-cyclopropylpyrimidine-4-carboxylic acid (1.6 g). The crude intermediate was heated at 140° C. for 8 minutes to give a brown sticky oil that was then partly dissolved in dichloromethane. The solution was decanted from the mixture and concentrated to give the subtitle compound as an oil (673 mg).

Provenance & Evidence