2,4-Bis(4-phenoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane → 1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

Participants

Reaction Steps

To a solution of N-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)cyclohexanecarboxamide (0.081 g, 0.196 mmol) in THF (1 mL) at rt was added 2,4-bis(4-phenoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (0.104 g, 0.196 mmol, TCI). After about 15 h at rt, the mixture was concentrated under reduced pressure. The residue was suspended in EtOAc/DCM (1:1) and filtered through a plug of silica gel (5 g) eluting with EtOAc/DCM (1:1, approximately 100 mL). The filtrate was concentrated under reduced pressure to provide a residue. The residue was dissolved in THF (1 mL) and mercury(II) acetate (0.0626 g, 0.196 mmol) was added. After about 30 min at rt, additional mercury(II) acetate (0.0626 g, 0.196 mmol) was added. After about 4 h at rt, the mixture was diluted with EtOAc, filtered, concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with a gradient of 50 to 95% EtOAc in heptane to provide 1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.020 g, 25%): LC/MS (Table 2, Method a) Rt=2.77 min; MS m/z: 395 (M+H)+.

Provenance & Evidence