Benzoyl chloride → HCID 67251365, compound

Participants

Reaction Steps

To 40 mL of dichloromethane, 4-n-propylamino-5-cyano-2-methylthiopyrimidine obtained in Step 1 was dissolved, then mCPBA-dichloromethane solution (0.50 mol/L, 25 mL, 12.5 mmol) was added thereto over 5 minutes, followed by stirring at room temperature for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then the solvent evaporated under reduced pressure. The residue was dissolved in THF (40 mL), then 2-(4-pyridyl)ethylamine (1.47 g, 12.0 mmol) was added thereto, followed by stirring at room temperature for 12 hours. After completion of the reaction was confirmed by thin-layer chromatography, chloroform (80 mL), benzoylchloride polymer bound [about 2.5 mmol/g, 4.6 g, Canadian Journal of Chemistry, Vol. 55, p. 3351 (1977)] and poly(4-vinylpyridine) (4.6 g) were added thereto, followed by further stirring at room temperature for 12 hours. After resins in the reaction mixture were filtered out, the filtrate was concentrated to give 5-cyano-4-n-propylamino-2-[2-(4-pyridyl)ethylamino]pyrimidine [Compound (Y) in which R1 is n-propylamino and R1 is 2-(4-pyridyl)ethylamino].

Provenance & Evidence