2-Aminopyrimidine → 2,6-dichloro-N-(2-(pyrimidin-2-ylamino)pyridin-4-yl)benzamide

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Reaction Steps

To a microwave tube were added N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.120 g, 0.347 mmol), 2-aminopyrimidine (0.040 g, 0.42 mmol), Pd2(dba)3 (0.030 g, 0.035 mmol), XantPhos (0.040 g, 0.070 mmol), Cs2CO3 (0.23 g, 0.70 mmol) and dioxane (2 mL). The mixture was degassed with N2 for 5 min. The resulting mixture was irradiated in a microwave reactor at 140° C. for 50 min and then cooled to room temperature. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was dissolved in DMF and purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired product as a white solid (15 mg, 12% yield). 1H NMR (500 MHz, MeOH-d4): δ 8.72 (s, 1H), 8.56 (d, J=4.5 Hz, 2H), 8.21 (d, J=5.5 Hz, 2H), 7.53-7.45 (m, 4H), 6.95 (t, J=5.0 Hz, 1H). LCMS (ESI) m/z: 360.0 [M+H+].

Provenance & Evidence