Triethylamine → HCID 86712638, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl 4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzylcarbamate (A12) (500 mg, 1.24 mmol), CuI (12 mg, 0.06 mmol), PPh3 (16 mg, 0.06 mmol), and Et3N (346 μL, 2.28 mmol) in DMF (3 mL) was sonicated for 5 minutes before the addition of PdCl2(PPh3)2 (44 mg, 0.06 mmol) and methyl 2-(2-ethynylphenyl)acetate (K1) (324 mg, 1.86 mmol). The resulting mixture was heated under microwave irradiation at 120° C. for 20 minutes then adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to yield a yellow solid. The solid was suspended in toluene and the resulting suspension sonicated for 10 minutes. The resulting suspension was filtered and the filter cake dried to give the title compound A13 as a yellow solid (412 mg, 61%); 1H NMR (400 MHz, d6-DMSO) δ 10.44 (s, 1H), 8.82 (s, 1H), 7.68 (d, J=8.4 Hz, 2H), 7.63 (d, J=7.6 Hz, 1H), 7.58-7.52 (m, 1H), 7.50-7.40 (m, 2H), 7.36 (t, J=6.0 Hz, 1H), 7.22 (d, J=8.5 Hz, 2H), 4.10 (d, J=6.0 Hz, 2H), 3.96 (s, 2H), 3.62 (s, 3H), 1.40 (s, 9H). LCMS-A: rt 6.497 min; m/z 539 [M−1]−.

Provenance & Evidence