Cesium carbonate → Methyl 1-(4-(4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-ylamino)phenyl)cyclobutylcarbamate

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(2-(2-(2-chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide (K6) (150 mg, 0.518 mmol), Pd(OAc)2 (11.6 mg, 0.052 mmol), Xantphos (45.0 mg, 0.078 mmol), Cs2CO3 (486 mg, 1.49 mmol) and methyl 1-(4-aminophenyl)cyclobutylcarbamate (A119) (125 mg, 0.569 mmol) in 1,4-dioxane (4.0 mL) was heated under microwave irradiation for 10 minutes at 150° C. The resulting mixture was filtered through Celite, and washed with EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by semi preparative HPLC to give the title compound 29 (86 mg, 35%); 1H NMR (300 MHz, CDCl3): δ 8.17 (br s, 1H), 7.56 (m, 2H), 7.42 (m, 2H), 7.28 (4H, obscured by solvent peak), 5.65 (br s, 1H), 5.42 (br s, 1H), 5.30 (br s, 1H), 3.70 (s, 2H), 3.61 (s, 3H), 3.13 (m, 2H), 2.99 (m, 2H), 2.57 (s, 3H), 2.12-1.62 (m, 6H). LCMS-B: rt 6.28 min; m/z 474.2 [M+H]+.

Provenance & Evidence