Reaction #69019

Reaction equation

N-(4-(3-bromo-1H-1,2,4-triazol-1-yl)phenyl)-4-(3-morpholinophenyl)pyrimidin-2-amine

tributyl(vinyl)stannane

toluene

→

desired product

4-(3-Morpholinophenyl)-N-(4-(3-vinyl-1H-1,2,4-triazol-1-yl)phenyl)pyrimidin-2-amine

Solvents

DMF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled down to room temperature
2. 2
   OtherPurification of this material by column chromatography on silica gel (40% EtOAc/hexane)

Procedure

A mixture of N-(4-(3-bromo-1H-1,2,4-triazol-1-yl)phenyl)-4-(3-morpholinophenyl)pyrimidin-2-amine (0.024 g, 0.05 mmol), tributyl(vinyl)stannane (0.032 g, 0.10 mmol), Pd(PPh3)4 (0.012 g, 0.01 mmol), toluene (0.4 mL) and DMF (0.1 mL) was heated in a sealed tube at 120° C. with microwave irradiation for 1 h. The reaction mixture was cooled down to room temperature. Purification of this material by column chromatography on silica gel (40% EtOAc/hexane) provided the desired product as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.43 (d, 1H), 8.36 (s, 1H), 7.80 (d, 2H), 7.59 (d, 2H), 7.37 (m, 4H), 7.14 (d, 1H), 7.01 (dd, 1H), 6.75 (dd, 1H), 6.27 (d, 1H), 5.51 (d, 1H), 3.84 (m, 4H), 3.20 (m, 4H). MS (ESI) 426.29 (M+H).

Source