Hydrogen Peroxide → HCID 70005572, compound

HRID 1267795Notes

Reaction equation

HRID 1267795 reaction equation
[C:1]([OH:7])([C:3](F)(F)F)=O.[NH2:8][C:9]1[N:13]([C@H:14]2[O:20][C@@H:19]([CH2:21][OH:22])[C@H:17]([OH:18])[C@@H:15]2[OH:16])[N:12]=[C:11]([C:23]#[N:24])C=1C#N.OO.[NH4+:29].[OH-:30]>>[NH2:8][C:9]1[N:13]([C@H:14]2[O:20][C@@H:19]([CH2:21][OH:22])[C@H:17]([OH:18])[C@@H:15]2[OH:16])[N:12]=[C:11]([C:23]([NH2:24])=[O:30])[C:3]=1[C:1]([NH2:29])=[O:7]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 53826353HCID 53826353, compound

Product 1

HCID 70005572HCID 70005572, compoundYield 68%

Procedure

The TFA salt of 5-amino-1-β-L-ribofuranosylpyrazole-3,4-dicarbonitrile (28) (2.60 g, 10.0 mmol) was dissolved in conc. NH4OH (28%, 100 mL) and treated with H2O2 (30%, 15 mL). The reaction mixture was stirred at room temperature in a pressure bottle for 12 h, and then evaporated to dryness. The residue was co-evaporated with MeOH (3×50 mL). The crude product was crystallized from a mixture of EtOH/water to give 2.0 g (68%) of (29): mp×° C.; 1H NMR (Me2SO-d6) δ 3.60 (m, 2H, C5.CH2) 3.87 (m, 1H, C4.H), 4.18 (m, 1H, C3.H), 4.54 (m, 1H, C2.H), 4.91 (t, 1H, C5.OH), 5.03 and 5.38 (2d, 2H, C2′,3′OH), 5.69 (d, 1H, C1′H), 6.99 (br s, 3H, NH2 and CONH(H)), 7.72 and 7.78 (2s, 2H, CONH2), and 9.65 (d, 1H, CON(H)H). Anal. Calc. for C10H15N5O6 (301.26): C, 39.87; H, 5.03; N, 23.25. Found: C, 39.72; H, 5.40; N, 23.61.

Workup

  1. customevaporated to dryness
  2. customThe crude product was crystallized from a mixture of EtOH/water

Sources & evidence

ORD record
ord-bb60b779ee53406499819e5273cd8056
Source dataset
uspto-grants-2003_04
Patent number
US06552183B1

Reaction notes

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