1,3-Bis(diphenylphosphino)propane → 6-(4-tert-butyl-phenyl)-5H-pyrazolo[1,5-a]pyrazin-4-one

HRID 2272958노트

반응식

HRID 2272958 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=[O:22])[C:14]3[N:15]([N:17]=[C:18](C=O)[CH:19]=3)[CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.O.O.[Rh](Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:12][C:13](=[O:22])[C:14]3[N:15]([N:17]=[CH:18][CH:19]=3)[CH:16]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 898261546-(4-Tert-butyl-phenyl)-4-oxo-4,5-dihydro-pyrazolo[1,5-a]pyrazine-2-carbaldehyde

생성물 1

HCID 898262006-(4-tert-butyl-phenyl)-5H-pyrazolo[1,5-a]pyrazin-4-one

시약·촉매·용매 1

HCID 11459718Rhodium chloride trihydrate촉매

반응 조건

온도
160 °C

실험 절차

140 mg (0.473 mmol) 6-(4-tert-butyl-phenyl)-4-oxo-4,5-dihydro-pyrazolo[1,5-a]pyrazine-2-carbaldehyde are dissolved in 1 ml diethyleneglycoldimethylether. 12 mg (0.028 mmol) 3-diphenylphosphanylpropyl(diphenyl)phosphane and 3.7 mg (0.014 mmol) rhodium(III)-chloride trihydrate are added. The reaction mixture is stirred for 42 hours at 160° C. The mixture is cooled to room temperature and partitioned between dichloromethane and water. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 6-(4-tert-butyl-phenyl)-5H-pyrazolo[1,5-a]pyrazin-4-one (“A15”) as colourless crystals; HPLC/MS: 1.88 (C), [M+H] 268.

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-ca15a3546ead4bbe849d1fd38de7d3ad
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120805B2

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