Reacción #159851

Ecuación de reacción

6-[4-(methylsulfonyl)phenyl]-5-phenyl-4-piperazin-1-yl-2-(trifluoromethyl)pyrimidine

thiophene-2-carboxylic acid

EDCI

HOBt

→

title compound

Rendimiento 48.6%

6-[4-(methylsulfonyl)phenyl]-5-phenyl-4-[4-(2-thienyl carbonyl)piperazin-1-yl]-2-(trifluoromethyl)pyrimidine

Rendimiento 48.6%

Disolventes

DMF

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwas stirred for 18 hours
2. 2
   Lavadothe organic layer was washed successively with water, 10% sodium bi carbonate solution (100 ml) and brine (100 ml) respectively
3. 3
   Secadodried over anhydrous sodium sulphate
4. 4
   OtroEvaporation of the solvent and purification by column chromatography (0.4% MeOH: DCM)

Procedimiento

To a solution of 6-[4-(methylsulfonyl)phenyl]-5-phenyl-4-piperazin-1-yl-2-(trifluoromethyl)pyrimidine (0.2 g, 0.43 mmol, prepared according to the procedure described in preparation 2) in DMF (20 ml) was added thiophene-2-carboxylic acid (0.149 g, 0.78 mmol) under stirring at 37° C. and then after 10 minutes EDCI (0.149 g, 0.78 mmol), and HOBt (0.023 g, 0.173 mmol) were added. Further TEA (0.179 ml, 2.9 mmol) was added to the resultant clear solution and it was stirred for 18 hours. Subsequently the reaction mixture was diluted with ethyl acetate (50 ml) and the organic layer was washed successively with water, 10% sodium bi carbonate solution (100 ml) and brine (100 ml) respectively and dried over anhydrous sodium sulphate. Evaporation of the solvent and purification by column chromatography (0.4% MeOH: DCM) gave the title compound (0.12 g, yield 48.6%); m.p. 189-194° C. 1H-NMR (CDCl3) δ: 2.98 (s, 3H), 3.4-3.41 (t, 4H), 3.66-3.68 (t, 4H), 7.02-7.77 (m, 12H); MS m/z: 573.2 (M++1).

Fuente