Sodium Iodide → HCID 60204461, compound

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (82 mg, 0.72 mmol) was added to a mixture of 1-(2-(4-(5-(4-fluorobenzyl)-4-(2-hydroxyethyl)thiophen-2-yl)-5-bromopyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (200 mg, 0.36 mmol) and diisopropylethylamine (93 mg, 0.72 mmol) in dichloromethane (10 mL) at 0° C. After stirring at 0° C. for 5 h, the solvent was removed in vacuo and 5 mL of N-methylpyrrolidine, a catalytic amount of sodium iodide and (S)-pyrrolidin-2-ylmethanol (0.3 g, 2.97 mmol) were added. The mixture was heated at 100° C. for 15 h and then cooled to rt. 50 mL of water was added and the mixture extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (3×50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the product purified by flash chromatography eluting with methanol (1M, ammonia)/dichloromethane (1:20) to give the title compound as a slightly yellow solid (105 mg, 46%). MS (M+H)+ 645/647.

Provenance & Evidence