Sodium periodate → HCID 16743592, compound

HRID 2042266Notes

Reaction equation

HRID 2042266 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]3[CH2:15][C:14](CO)([OH:16])[CH2:13]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]3[CH2:13][C:14](=[O:16])[CH2:15]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 576810553-(8-Chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)-1-(hydroxymethyl)cyclobutanol

Product 1

HCID 16743592HCID 16743592, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(8-chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)-1-hydroxymethylcyclobutanol (4.08 g, 0.01 μmol) in THF (120 mL) and water (40 mL) was charged with sodium periodate (2.8 g, 0.013 mol) at 0° C. The reaction warmed to rt and stirred for 5 h. The reaction mixture was diluted with ethyl acetate and then washed with brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound as a yellow solid; 1H NMR (CDCl3, 400 MHz) δ 7.56 (1 H, d, J=4.94), 7.32 (1 H, d, J=4.98), 3.64 (5 H, m); MS (ES+): m/z 347.82 and 349.85 [MH+]; HPLC: tR=2.89 min. (OpenLynx, polar—5 min.).

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-926cc4a3206b4a08b25b9b84740a3c1a
Source dataset
uspto-grants-2013_11
Patent number
US08586546B2

Reaction notes

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