Sodium periodate → HCID 16743592, compound

HRID 1878846Notes

Reaction equation

HRID 1878846 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-α]pyrazin-3-yl)-1-hydroxymethylcyclobutanol (4.08 g, 0.011 mol) 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 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-fd8a373518f645b58397048388b3da80
Source dataset
uspto-grants-2012_11
Patent number
US08314111B2

Reaction notes

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