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

HRID 2272957노트

반응식

HRID 2272957 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c17acb83a9b4feb802b2de04ccb51c5
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120805B2

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