tert-Butanol → HCID 58592848, compound

HRID 642863Notes

Reaction equation

HRID 642863 reaction equation
[CH:1]([C:3]1[CH:12]=[N:11][C:6]2=[N:7][CH:8]=[CH:9][N:10]=[C:5]2[CH:4]=1)=C.CC([OH:17])(C)C.I([O-])(=O)(=O)=O.[Na+]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[N:10]1[CH:9]=[CH:8][N:7]=[C:6]2[N:11]=[CH:12][C:3]([CH:1]=[O:17])=[CH:4][C:5]=12

Participants

7

Reactant 3

HCID 6386tert-ButanolHCID 23667635Sodium periodateHCID 58592807HCID 58592807, compound

Product 1

HCID 58592848HCID 58592848, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

7-Vinyl-pyrido[2,3-b]pyrazine (68 mg, 0.43 mmol) was dissolved in dioxane (4 ml) and water (5 ml). OsO4 (0.227 ml of a 2.5% t-BuOH solution, 0.024 mmol) was added, followed by sodium periodate (276 mg, 1.3 mmol). The reaction mixture was allowed to stir at room temperature. After 2 h, the reaction was judged complete by TLC, and the reaction mixture was partitioned between ethyl acetate and brine. The brine was removed and washed one additional time with ethyl acetate. The combined ethyl acetate extracts were washed again with brine, dried using MgSO4, and concentrated under vacuum to yield the title product (65 mg, 95%) as a dark, nearly black, solid. 1H NMR (DMSO-d6): δ=10.37 (s, 1H), 9.55 (d, 1H, J=2.2 Hz,), 9.28 (d, 1H, J=1.7 Hz), 9.21 (d, 1H, J=1.7 Hz), 9.10 (d, 1H, J=2.2 Hz). Calculated mass=159.15, [M+H]+=160. HPLC Method D: 97.5% @ 210-370 nm; 97.9% @ 318 rm; RT=2.4 min.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and brine
  2. customThe brine was removed
  3. washwashed one additional time with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed again with brine
  5. customdried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-704eb97536a045c88594f71bc67ec27c
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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