Bicarbonate Ion → HCID 86669127, compound

Participants

Reaction Steps

To a solution of 2-chloro-pyrimidine-4-carboxylic acid (200 mg, 1.3 mmol) in dichloromethane (10 ml) cooled in an ice/water bath was added oxalyl chloride (0.7 ml) and dimethylformamide (3 drops). The reaction was incomplete after 45 minutes so a further portion of oxalyl chloride was added (0.7 ml) and the reaction allowed to proceed at room temperature for a further hour. The reaction was then concentrated and to the crude acid chloride was added pyridine (0.1 ml) and methylamine hydrochloride (0.16 g, 1.9 mmol). After stirring for 3 hours a further portion of both reagents were added and the reaction left to stir overnight. To the reaction was added dilute bicarbonate solution and the mixture was extracted with dichloromethane. The organic liquors were concentrated to furnish the title compound as a yellow solid (150 mg). 1H NMR (400 MHz, DMSO-d6): 9.01 (1H, d), 8.99-8.88 (1H, m), 8.01 (1H, d), 2.83 (3H, d).

Provenance & Evidence