Dimethylamine → HCID 4190857, compound

Participants

Reaction Steps

4,6-dichloro-2-methylmercaptopyrimidine (10.0 g, 51 mmol) and diisopropyl ethylamine (17.5 ml, 102 mmol) was dissolved in tetrahydrofuran (400 ml), and a 50% aqueous dimethylamine solution (7.6 ml, 84 mmol) was dripped over the course of 1 hour into this solution under ice cooling. After this mixture liquid was agitated overnight at room temperature, water was added and extraction was carried out 2 times with ethyl acetate. After washing the organic layer with saturated saline, drying was done with MgSO4, the solvent was distilled away under reduced pressure, and 6-chloro-4-dimethylamino-2-methylmercaptopyrimidine was obtained. This was used for the next reaction without separation or refinement. Morpholine (100 ml) was added to this, and it was agitated overnight at 100 degrees Celsius. After allowing to cool, water was added and extraction was carried out 2 times with dichloromethane. After washing the organic layer with saturated saline, drying was done with MgSO4, the solvent was distilled away under reduced pressure. The residue was washed with ether and 11.3 g of coarse crystals of 4-dimethylamino-2-methylsulfanyl-6-morpholinopyrimidine was obtained (2 step yield: 87%).

Provenance & Evidence