Potassium Carbonate → 4-(5-{3-[(5-Chloropyrimidin-2-yl)amino]-5-methylphenyl}-1,3-thiazol-2-yl)-1,4-diazepan-2-one

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with a stir bar, 4-[5-(3-amino-5-methylphenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one (100 mg, 0.331 mmol), 2,5-dichloropyrimidine (49.3 mg, 0.331 mmol), potassium carbonate (91 mg, 0.661 mmol), Pd2 dba3 (30.3 mg, 0.033 mmol), and XPhos (79 mg, 0.165 mmol). The tube was evacuated and backfilled with argon three times. Fully degassed t-amyl alcohol (1.1 ml) was added, the tube was sealed and heated at 90° C. for overnight. The slurry was then cooled to room temperature, diluted with methanol, absorbed onto 2 g of silica, and purified via silica gel chromatography (0-20% methanol in ethyl acetate) to afford 4-(5-{3-[(5-chloropyrimidin-2-yl)amino]-5-methylphenyl}-1,3-thiazol-2-yl)-1,4-diazepan-2-one (66 mg, 0.159 mmol, 48.1% yield) as a bright yellow solid. MS APCI: [M+H]+ m/z 415.1. 1H NMR (500 MHz, DMSO) δ 9.80 (s, 1H), 8.55 (s, 2H), 7.60 (s, 2H), 7.46 (s, 1H), 7.41 (s, 1H), 6.93 (s, 1H), 4.16 (m, 2H), 3.78 (m, 2H), 3.20 (m, 2H), 2.26 (s, 3H), 1.78 (m, 2H). rhSyk=+++.

Provenance & Evidence