Triacetoxyperiodinane → 6-(4-Tert-butyl-phenyl)-4-oxo-4,5-dihydro-pyrazolo[1,5-a]pyrazine-2-carbaldehyde

HRID 2272957Notes

Reaction equation

HRID 2272957 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([C:33]2[NH:34][C:35](=[O:44])[C:36]3[N:37]([N:39]=[C:40]([CH2:42][OH:43])[CH:41]=3)[CH:38]=2)=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]>ClCCl.CN(C=O)C>[C:23]([C:27]1[CH:28]=[CH:29][C:30]([C:33]2[NH:34][C:35](=[O:44])[C:36]3[N:37]([N:39]=[C:40]([CH:42]=[O:43])[CH:41]=3)[CH:38]=2)=[CH:31][CH:32]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 717654606-(4-tert-butyl-phenyl)-2-hydroxymethyl-5H-pyrazolo[1,5-a]pyrazin-4-one

Product 1

HCID 898261546-(4-Tert-butyl-phenyl)-4-oxo-4,5-dihydro-pyrazolo[1,5-a]pyrazine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

599 mg (1.41 mmol) Dess-Martin periodinane is added to a solution of 140 mg (0.471 mmol) 6-(4-tert-butyl-phenyl)-2-hydroxymethyl-5H-pyrazolo[1,5-a]pyrazin-4-one in 5 ml dichloromethane and 1 ml DMF. The reaction mixture is stirred at ambient temperature for 18 hours. The reaction mixture is filtered and the filtrate is washed with saturated sodium thiosulfate solution and with saturated sodium hydrogen carbonate solution. The organic phase is dried over sodium sulfate and evaporated. The residue is triturated with tert-butylmethylether, the solid is filtered off and dried under vacuum to give 6-(4-tert-butyl-phenyl)-4-oxo-4,5-dihydro-pyrazolo[1,5-a]pyrazine-2-carbaldehyde as light yellow crystals; HPLC/MS: 1.93 (C), [M+H] 296.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe filtrate is washed with saturated sodium thiosulfate solution and with saturated sodium hydrogen carbonate solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customThe residue is triturated with tert-butylmethylether
  6. filtrationthe solid is filtered off
  7. customdried under vacuum

Sources & evidence

ORD record
ord-9c17acb83a9b4feb802b2de04ccb51c5
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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