Water → N9-(3-Azidopropyl)-2-amino-6-chloropurine

Participants

Reaction Conditions

Reaction Steps

N9-(3-Chloropropyl)-2-amino-6-chlorpurine (21, 2.56 g, 10.40 mmol) and sodium azide (811 mg, 12.48 mmol) are dissolved in 25 mL DMSO and stirred at 80° C. for 16 h. After cooling to room temperature, the reaction mixture is poured into 150 mL of water and extracted with CH2Cl2. The combined organic phases are washed with water, dried over MgSO4 and evaporated in vacuo. The residue is purified by flash column chromatography (dichloromethane/methanol 50:1 to 10:1) to yield the title compound as a colorless solid (650 mg, 2.57 mmol, 24%). 1H-NMR (400 MHz, DMSO-d6): δ=8.12 (s, 1H, H-8), 6.89 (s, 2H, NH2), 4.10 (t, J=6.8, 2H, CH2), 3.38 (t, J=6.8, 2H, CH2), 2.05 (m, 2H, CH2) ppm. MS (ESI) m/z 253.0 [M+H]+.

Provenance & Evidence