N,N-Dimethylaniline → HCID 10933636, compound

Participants

Reaction Conditions

Reaction Steps

Phosgene (20 g, 202 mmol) was passed at 20-25° C. in the course of 45 min into a recipient vessel of ethyl acetate (120 ml). A solution of 2-amino4,6-dimethoxypyrimidine (15.6 g, 101 mmol) and N,N-dimethyl-aniline (26 ml, 203 mmol) in ethyl acetate (90 ml) was added dropwise at 25° C. in the course of 3 h. After 15 min, the suspension was aerated with nitrogen until it was free of phosgene, ethyl acetate (120 ml) was added and isopropanol (10 ml, 130 mmol) was added dropwise in the course of 10 min with cooling (20-25° C.). The reaction was filtered after 1 h, washed with ethyl acetate (3×20 ml) and the combined filtrates were extracted with hydrochloric acid (1.0 N, 2×30 ml) and water (2×30 ml). The solution was then concentrated and the product was crystallized from the residue; yield 19.2 g (80% of theory), m.p. 51-54° C.

Provenance & Evidence