Methyl iodide → HCID 21905823, compound

Participants

Reaction Steps

A suspension of 8-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-1-isopropyl-1,3,8-triazaspiro[4.5]decan-4-one 13A-1 (86 mg, 0.16 mmol) and methyl iodide (2 M in MTBE, 16 μl) in 1:1 tetrahydrofuran/dimethylformamide (2 ml) was treated with sodium hydride (60% dispersion in oil, 12 mg, 0.3 mmol). After stirring for 2 hours, the mixture was extracted from saturated aqueous sodium bicarbonate with ethyl acetate, dried (Na2SO4), concentrated (123 mg), and then purified by flash chromatography using 4% methanol to give title compound 25A-1 as an oil (87 mg, quantitative). A methylene chloride solution of the material was treated with excess 1 M HCl in ether, concentrated under a stream of nitrogen, and then triturated from ether to give the hydrochloride salt of compound 25A-1 (82 mg, 82% overall) as a colorless solid: +ESI MS (M+1) 550.2; 1H NMR (400 MHz, CD3OD) δ 8.34 (s, 1H), 7.60 (d, J=7.9 Hz, 1H), 7.51–7.39 (m, 5H), 7.31 (d, J=8.3 Hz, 2H), 4.76 (s, 2H), 4.14 (brs, 2H), 3.78 (brs, 1H), 2.96 (s, 3H), 2.28 (br s, 4H), 1.32 (d, J=6.2 Hz, 6H).

Provenance & Evidence