Diiodomethane → 6-Chloro-2-iodo-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purine

Participants

Reaction Steps

To a mixture of 117a (2.99 g, 10.0 mmol), CH2I2 (4.0 ml, 51.0 mmol), and CuI (1.91 g, 10.0 mmol) in THF was added isoamyl nitrite (4.0 mL, 30.0 mmol). The mixture was heated at reflux for 1.0 h and cooled to room temperature. The reaction mixture was partitioned between ethyl acetate and 1N aqueous HCl solution. The organic phase was washed with saturated aqueous NH4Cl, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 3:1 petroleum ether/ethyl acetate to afford 117b (2.02 g, 49%) as a yellow solid. MS-ESI: [M+H]+ 411.0

Provenance & Evidence