Potassium Acetate → HCID 59627379, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-(4-Methoxybenzyl)-6-bromo-9H-purine (2.7 g, 8.5 mmol), 2-fluoropyridin-3-ylboronic acid (1.8 g, 13 mmol) and potassium acetate (2.5 g, 25 mmol) in 1-butanol (50 mL) and water (10 mL) was purged with Ar (vacuum/purge three times) to remove oxygen, then PdCl2(PtBu2Ph)2 (0.063 g, 0.10 mmol) was added. The reaction mixture was stirred in a 100° C. oil bath for 45 min. The reaction mixture was allowed to cool to RT and diluted with Et2O (300 mL). The mixture was washed with water (2×100 mL), brine (50 mL), dried over Na2SO4, and filtered. Some product precipitated before the filtration so the Na2SO4 was washed with 3:1 CHCl3:IPA to dissolve all product. The combined filtrate was concentrated in vacuo to ˜50 mL as a suspension. The suspension was diluted with Et2O (200 mL) and hexane (200 mL) and the solid collected by suction filtration. The solid was washed with hexane (50 mL) and dried under a stream of N2 with vacuum suction for 14 h to afford 2.39 g (crop 1) as a pale orange fine crystalline solid. The mother liquors were concentrated in vacuo to ˜100 mL to afford a second crop of product. The second crop was collected by suction filtration, washed with hexane (100 mL) and dried under a stream of N2 as above to provide 200 mg (crop 2) as a pale orange fine crystalline solid. MS (ESI, pos. ion) m/z: 336.1 [M+H]+.

Provenance & Evidence