Biphenyl → HCID 58946484, compound

HRID 1038010Notes

Reaction equation

HRID 1038010 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:21][C@H:22]1[CH2:27][NH:26][CH2:25][CH2:24][NH:23]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>[CH3:14][C:11]1[CH:10]=[N:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:26]3[CH2:25][CH2:24][NH:23][C@@H:22]([CH3:21])[CH2:27]3)=[CH:3][CH:4]=2)=[N:13][CH:12]=1

Participants

9

Reactant 4

HCID 7095BiphenylHCID 10796Cesium carbonateHCID 7679462-(4-bromophenyl)-5-methylpyrimidineHCID 27342192-Methylpiperazine, (S)-

Product 1

HCID 58946484HCID 58946484, compound

Reagents, catalysts & solvents 4

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

Procedure

A mixture of 2-(4-bromophenyl)-5-methylpyrimidine 78 (250 mg, 1.008 mmol), palladium acetate (50 mg), cesium carbonate (400 mg, 1.23 mmol), (S)-2-methyl piperazine (200 mg, 2 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 79 as a white solid. (220 mg. 81%) ESMS (MH, 269).

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-1a7cd613e220452e9c72bd5dcae73d1a
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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