Piperazine → HCID 59511338、化合物

HRID 1038012ノート

反応式

HRID 1038012 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1(C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C(Cl)Cl.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:21]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=3)=[CH:4][CH:3]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

参加物

9

反応物 4

HCID 4837PiperazineHCID 7095BiphenylHCID 10796Cesium carbonateHCID 595113755-(4-Bromophenyl)pyrimidin-2-amine

生成物 1

HCID 59511338HCID 59511338、化合物

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 5-(4-bromo-phenyl)-pyrimidin-2-ylamine (100 mg, 0.401 mmol), palladium acetate (20 mg, 0.089 mmol), cesium carbonate (200 mg, 0.62 mmol), piperazine (100 mg, 1.16 mmol) and 2-di-t-butylphosphino)-biphenyl (50 mg, 0.167 mmol) was stirred in dioxane:water (10 ml, v/v 5:1) at reflux temperature for 4 hours. The reaction was cooled, diluted with MeCl2 (100 ml) and H2O (50 ml). The organic layer was separated, dried (MgSO4), filtered and solvent evaporated. The residue was purified by chromatography eluting with 100% EtOAc then with 10% v/v MeOH/EtOAc/NH4OH yielding product 82 as a white solid. (70 mg. 68%) ESMS (MH, 256).

後処理

  1. temperatureThe reaction was cooled
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customThe residue was purified by chromatography
  7. washeluting with 100% EtOAc

出典と根拠

ORDレコード
ord-c15044741d9b418cbe8cfeb46683003a
出典データセット
uspto-grants-2013_10
特許番号
US08546404B2

反応ノート

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