Cesium carbonate → tert-Butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(2-(2-(2-chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide (K6) (0.150 g, 0.518 mmol), tert-butyl 3-(4-aminophenyl)azetidine-1-carboxylate (A77) (0.141 g, 0.569 mmol), Pd(OAc)2 (2.3 mg, 0.010 mmol), Cs2CO3 (0.506 g, 1.55 mmol) and Xantphos (11.9 mg, 0.021 mmol) in 1,4-dioxane (2 mL) was heated under microwave irradiation at 100° C. for 1.5 hours. The resulting mixture was dry loaded onto silica gel and purified using silica gel column chromatography (CombiFlash Rf, 12 g SiO2 Cartridge, 0-5% MeOH in DCM) to give the title compound A123 as a light orange foam (0.087 g, 33%); 1H NMR (300 MHz, CDCl3) δ 8.12 (s, 1H), 7.59 (d, J=8.5 Hz, 2H), 7.53 (s, 1H), 7.26-7.28 (m, 6H), 5.59 (brs, 2H), 4.32 (t, J=8.7 Hz, 2H), 3.97 (dd, J=6.0, 8.4 Hz, 2H), 3.70-3.76 (m, 3H), 3.08-3.13 (m, 2H), 2.90-2.98 (m, 2H), 2.13 (s, 3H), 1.48 (s, 9H). LCMS-B: rt 7.208 min; m/z 502 [M+H]+.

Provenance & Evidence