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

HRID 2272957ノート

反応式

HRID 2272957 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c17acb83a9b4feb802b2de04ccb51c5
出典データセット
uspto-grants-2015_09
特許番号
US09120805B2

反応ノート

読み込み中…