Sodium methanethiolate → N-(2,2-diphenylethyl)-2-(methylsulphanyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 2-chloro-N-(2,2-diphenylethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine (preparation 6) (49.7 g, 0.11 mol) in dry N,N-dimethylformamide (200 ml) was treated with sodium thiomethoxide (10 g, 0.14 mol) and the resulting mixture heated under an atmosphere of nitrogen at 100° C. for 1.5 hr. The mixture was then stirred at room temperature for 72 hr and then reheated to 100° C. for a further 2 hr. The reaction mixture was then cooled and diluted with water (1000 ml). A suspension was formed which was extracted with diethyl ether (×2). The combined organic extracts were washed sequentially with water and brine, dried with anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was dissolved in diethyl ether and the solvent removed under reduced pressure. This procedure was then repeated using pentane to afford the title compound as a foam (48.9 g).

Provenance & Evidence