Morpholine → HCID 44829125, compound

Participants

Reaction Steps

5-Iodouridine-5′-monophosphate 1 (292 mg, 0.65 mmol) was dissolved in dry DMSO, co-evaporated (3×) with dry DMF, and finally dissolved in 0.5 mL of dry DMSO. Morpholine (400 μL, 4.6 mmol) was added and the reaction mixture was stirred at room temperature for 5 min. Dipyridyl disulfide (500 mg, 2.3 mmol) and triphenylphosphine (600 mg, 2.3 mmol) were added in 5 min intervals, and the reaction mixture was stirred for another 60 minutes at room temperature. Upon quenching of the reaction with 0.1 M NaI in acetone a precipitate formed. The supernatant was removed, and the precipitate was washed repeatedly with cold acetone, to give 354 mg (99% yield) of 5-Iodouridine-5′-phosphoromorpholidate as a white powder. This material was used in the next step without further purification. δH (400 MHz, D2O) 3.04-3.16 (4H, m, H-Morpholine), 3.65-3.73 (4H, m, H-Morpholine), 4.00-4.15 (2H, m, H-5′), 4.24-4.26 (1H, m, H-4′), 4.27-4.32 (1H, m, H-3′), 4.36 (1H, t, J=5.4 Hz, H-2′), 5.94 (1H, d, J=5.8 Hz, H-1′), 8.17 (1H, s, H-6). δC (75.5 MHz, D2O) 64.3 (morpholine), 63.3 (d, J=5.4 Hz, C-5′), 66.3 (morpholine), 67.8 (C-5), 68.6 (C-3′), 73.2 (C-2′), 83.0 (d, J=8.4 Hz, C-4′), 88.2 (C-1′), 145.0 (C-6), 153.3 (C-2), 161.9 (C-4); OP (121.5 MHz, D2O) 11.0 ppm. m/z (ESI) 519.9968 [M+H]+, C13H19IN3O9P requires 519.9976.

Provenance & Evidence