Dimethylamine → HCID 14788029, compound

Participants

Reaction Steps

A solution of 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.5 g, 1.1 mmole) in 10 ml of dry tetrahydrofuran under argon at 0°-5° C. was treated with pyridine (1.0 ml, 12.6 mmole), then with phosgene (1.16 ml of 12.5% in benzene, 1.47 mmol). After 0.5 hours at 0°-5° C., dimethylamine (1 ml of 40% aqueous, excess) was added. Reaction was complete within 0.5 hours. The mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid, water and saturated brine. The aqueous washes were back extracted with fresh ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to give 0.6 g of essentially homogeneous product.

Provenance & Evidence