Sodium Bicarbonate → HCID 86704184, compound

Participants

Reaction Steps

A flask was filled with 2.02 g (10 mmol) of 2-amino-4,6-dichloro-5-(prop-2-yn-1-yl)pyrimidine and 10 ml of 2 mol·l1 (20 mmol) of a solution of the Vilsmeier-Haack-Arnold reagent in chloroform. The reaction mixture was refluxed for eight hours. Having been cooled to laboratory temperature, the reaction mixture was poured onto ice and rapidly neutralized by NaHCO3. The obtained mixture was quickly transferred into a separatory funnel and immediately extracted by 3×20 ml of chloroform. The organic fractions were connected and dried using MgSO4. According to TLC, the reaction mixture contained another substance besides 4,6-dichloro-2-{[(dimethylamino)methylene]amino}-5-(prop-2-yn-1-yl)pyrimidine. The acquired mixture was therefore separated by column chromatography with a hexane/ethyl-acetate mobile phase (80/20 to 50/50). After evaporation of the organic solvents, the isolated substances were 686 mg of 4,6-dichloro-2-{[(dimethylamino)methylene]amino}-5-(prop-2-yn-1-yl)pyrimidine, 317 mg of 4,6-dichloro-2-formamido-5-(prop-2-yn-1-yl)pyrimidine and 458 mg of 4,6-dichloro-5-(2-chloroallyl)-2-formamidopyrimidine, which is created by the addition of hydrochloric acid (developed during the reaction) to the triple bond present. The hydrolysis to 2-formamido derivatives did not occur until during the chromatography.

Provenance & Evidence