Potassium Carbonate → HCID 16129033, compound

Participants

Reaction Steps

4-Methyl-piperazine-1-carboxylic acid 4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl ester can be synthesized by the following procedure. A suspension of 4-methyl-piperazine-1-carboxylic acid 4-amino-phenyl ester (0.166 mmol) (from example 3i), 4-methoxy phenyl boronic acid (0.199 mmol), K2CO3 (0.36 mmol) and Pd(PPh3)4 (0.0166 mmol) in a 5:1 mixture of DME:H2O (1.5 mL) is heated at 80° C. for 10 min. The reaction mixture is cooled to rt, diluted with dichloromethane, washed with NH4Cl, and dried under reduced pressure. The crude is purified by a short silica column using a mixture 9.5:0.5:0.1=DCM:MeOH:NH4OH to afford 4-methyl-piperazine-1-carboxylic acid 4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl ester as white powder (86%). 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 2H), 7.57 (d, J=8.0 Hz, 2H), 7.37 (d, J=8.0 Hz, 2H), 7.12 (b.s, 1H), 7.0.2 (m, 2H), 6.95 (m, 2H), 3.79 (s, 3H), 3.71-3.69 (m, 4H), 2.51-2.50 (m, 4H). MS (m/z) (M+1)+ 420.2.

Provenance & Evidence