Hydrochloric Acid → 5-[5-Bromo-4-(4-hydroxy-butylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide

Participants

Reaction Steps

298 mg (1.0 mmol) of 4-(5-bromo-2-chloro-pyrimidin-4-ylsulfanyl)-butan-1-ol is dissolved in 2 ml of acetonitrile and added to a suspension of 172 mg (1.0 mmol) of 5-amino-pyridine-2-sulfonic acid amide (representation according to W. T. Caldwell, E. C. Kornfeld J Am. Chem. Soc. 1942, 64, 1695-1698) in 1 ml of acetonitrile, 0.25 ml of a 4 molar solution of hydrochloric acid in 1,4-dioxane as well as 0.25 ml of water. The reaction mixture is stirred under reflux for 24 hours. It is mixed with 1 ml of ethanol and stirred for another 24 hours under reflux. After cooling, the precipitate that is formed is filtered off, and the filtrate is concentrated by evaporation. The residue is purified by chromatography (Flashmaster II, DCM/MeOH 9:1). The crude product that is obtained is then purified by preoperative thin-layer chromatography. 43 mg (0.10 mmol, 10% of theory) of the product 5-[5-bromo-4-(4-hydroxy-butylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide is obtained

Provenance & Evidence