Water → HCID 58592764, compound

HRID 642869Notes

Reaction equation

HRID 642869 reaction equation
C([C:3]1[CH:4]=[CH:5][C:6]2[C:7]([N:14]=1)=[N:8][C:9](=O)[C:10](=O)[N:11]=2)=C.[C:15](O)(C)(C)C.I([O-])(=O)(=O)=O.[Na+].[OH2:26]>O1CCOCC1.[Os](=O)(=O)(=O)=O>[N:8]1[CH:9]=[C:10]([CH:15]=[O:26])[N:11]=[C:6]2[CH:7]=[N:14][CH:3]=[CH:4][C:5]=12

Participants

7

Reactant 4

HCID 962Water2×HCID 6386tert-ButanolHCID 23667635Sodium periodateHCID 68579213HCID 68579213, compound

Product 1

HCID 58592764HCID 58592764, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of the vinylpyridopyrazinedione above (0.14 g, 0.74 mMol) in dioxane (6 mL) and water (3 mL) was treated with 2.5% osmium tetroxide solution in t-butanol (0.38 mL, 37 μMol) and sodium periodate (0.48 g, 2.2 nMol). After stirring for 3 h the reaction mixture was diluted with water (20 mL) and the product was purified by reversed phase HPLC (method F) using nonbuffered mobile phase. The pure product was isolated as a solid (56 mg, 40%). 1H-NMR (DMSO-d6), δ=12.80 (bs, 1H), 12.20 (bs, 1H), 10.01 (s, 1H), 8.62 (d, 1H, J=1.8 Hz), 7.78 (d, 1H, J=1.8 Hz).

Workup

  1. customthe product was purified by reversed phase HPLC (method F)

Sources & evidence

ORD record
ord-bb87d92264b44818bc81e92d3cb923f2
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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