5-Nitro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone → 5-Nitro-1-beta-D-ribofuranosylpyridin-2(1H)-one

HRID 419783Notes

Reaction equation

HRID 419783 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:43])[N:8]([C@@H:10]2[O:32][C@H:31]([CH2:33][O:34]C(=O)C3C=CC=CC=3)[C@@H:21]([O:22]C(=O)C3C=CC=CC=3)[C@H:11]2[O:12]C(=O)C2C=CC=CC=2)[CH:9]=1)([O-:3])=[O:2]>N>[C@@H:10]1([N:8]2[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]2=[O:43])[O:32][C@H:31]([CH2:33][OH:34])[C@@H:21]([OH:22])[C@H:11]1[OH:12]

Participants

3

Reactant 1

HCID 112732675-Nitro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone

Product 1

HCID 666496085-Nitro-1-beta-D-ribofuranosylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A mixture of 5-nitro-1-(2′,3′,5′-tri-O-benzoyl-β-ribofuranosyl)-2-pyridone (10, R=Bz, Y=H, Z=CH; 100 mg, 0.17 mmol) and saturated methanolic ammonia (10 mL) was stirred at room temperature for 12 h. The mixture was concentrated to dryness, and the residue triturated with EtOH to precipitate 10 (R=Y=H, Z=CH), which was collected and recrystallized from water (37 mg, 81%) as a white solid. 1H NMR (DMSO-d6+D2O) δ 3.64 (m, 1H), 3.90 (m, 1H), 4.01 (m, 3H), 5.89 (s, 1H), 6.48 (d, J=10.4 Hz, 1H), 8.12 (dd, J=3.2, 10 Hz, 1H), 9.65 (d, J=3.2 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue triturated with EtOH
  3. customto precipitate 10 (R=Y=H, Z=CH), which
  4. customwas collected
  5. customrecrystallized from water (37 mg, 81%) as a white solid

Sources & evidence

ORD record
ord-e0e00f1c933d466e893aa2689309f616
Source dataset
uspto-grants-2012_01
Patent number
US08093380B2

Reaction notes

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