Piperazine → HCID 59511338, 화합물

HRID 1038012노트

반응식

HRID 1038012 반응식
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

참가 물질

9

반응물 4

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

생성물 1

HCID 59511338HCID 59511338, 화합물

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c15044741d9b418cbe8cfeb46683003a
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546404B2

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