Hydrogen Peroxide → HCID 70005572, compound

HRID 1368710Notes

Reaction equation

HRID 1368710 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) δ3.60 (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-033cc671a1cb4abd80e752955107de77
Source dataset
uspto-grants-2003_06
Patent number
US06573248B2

Reaction notes

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