Piperazine → HCID 59511338, compound

HRID 1157165Notes

Reaction equation

HRID 1157165 reaction equation
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

Participants

9

Reactant 4

HCID 4837PiperazineHCID 7095BiphenylHCID 10796Cesium carbonateHCID 59511375HCID 59511375, compound

Product 1

HCID 59511338HCID 59511338, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0ed7b53f7c5748fdb2e848d32212b567
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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