Sodium periodate → HCID 16743592, compound

HRID 448976Notes

Reaction equation

HRID 448976 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.CCOC(C)=O>[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, 0.011 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 5 h. The reaction mixture was diluted with EtOAc 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 (1H, d, J=4.94 Hz), 7.32 (1H, d, J=4.98 Hz), 3.64 (5H, 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-caea81116b0342b9ad56c50cefb5b2a4
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…