Reacción #78382

Ecuación de reacción

methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate

cyanamide

ethyl acetate

→

methyl 2-amino-4-(4-fluorophenyl)-6-isopropylpyrimidine-5-carboxylate

Rendimiento 8.4%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated to reflux
2. 2
   FiltraciónThe undissolved solid was filtered off
3. 3
   OtroThe organic phase was separated off
4. 4
   Extracciónthe aqueous phase was extracted with ethyl acetate (2×5 ml)
5. 5
   SecadoThe combined organic phases were dried over magnesium sulphate
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude product (0.97 g) was purified by flash chromatography on silica gel (eluent: methylene chloride)

Procedimiento

A suspension of 1.33 g of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate (5.00 mmol) in 4.20 g of 50% strength aqueous cyanamide solution (50.0 mmol) was heated to reflux. After 17 h, it was cooled to room temperature and treated with ethyl acetate (5 ml) and water (5 ml). The undissolved solid was filtered off. The organic phase was separated off and the aqueous phase was extracted with ethyl acetate (2×5 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo. The crude product (0.97 g) was purified by flash chromatography on silica gel (eluent: methylene chloride). 121.6 mg of methyl 2-amino-4-(4-fluorophenyl)-6-isopropylpyrimidine-5-carboxylate were obtained in the form of a colourless solid.

Fuente