Sodium hydride → 5-(4-phenoxyphenyl)-7-(1,4-dioxaspiro[4.5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

関与物質

反応条件

反応手順

Sodium hydride (0.26 g of a 60% dispersion in mineral oil) was added to a mixture of 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.94 g) in dimethylformamide 950 ml) at ambient temperature with stirring. The mixture was stirred until the evolution of hydrogen ceased and then 8-tosyloxy-1,4-dioxaspiro[4,5]decane (2.0 g, prepared as described in U.S. Pat. No. 4,360,531 from 1,4-dioxaspiro[4,5]decan-8-one, (which was prepared according to J. Med. Chem. 1992, 22460) was added. The mixture was heated at 120° C. for 5 hours under nitrogen, cooled to ambient temperature, quenched with water and extracted with ethyl acetate to give a residue which was purified by flash column chromatography on silica using ethyl acetate followed by ethyl acetate containing increasing amounts of methanol up to 6% to give 5-(4-phenoxyphenyl)-7-(1,4-dioxaspiro[4,5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 193-194° C.

情報源と証拠