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

HRID 2272958ノート

反応式

HRID 2272958 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 11459718Rhodium chloride trihydrate触媒

反応条件

温度
160 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ca15a3546ead4bbe849d1fd38de7d3ad
出典データセット
uspto-grants-2015_09
特許番号
US09120805B2

反応ノート

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