Sodium Bicarbonate → 4-[4-(5-Bromo-3-chloro-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(S)-methyl-pyrrolidin-1-yl)-pyrimidine

HRID 1444147Notes

Reaction equation

HRID 1444147 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([N:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[CH3:20])[N:3]=1.[Br:21][C:22]1[CH:23]=[C:24]([Cl:35])[C:25]([N:28]2[CH2:33][CH2:32][NH:31][C@H:30]([CH3:34])[CH2:29]2)=[N:26][CH:27]=1.C([O-])(O)=O.[Na+]>CCO>[Br:21][C:22]1[CH:23]=[C:24]([Cl:35])[C:25]([N:28]2[CH2:33][CH2:32][N:31]([C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=4)[N:5]=[C:4]([N:15]4[CH2:19][CH2:18][CH2:17][C@@H:16]4[CH3:20])[N:3]=3)[C@H:30]([CH3:34])[CH2:29]2)=[N:26][CH:27]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11500246HCID 11500246, compoundHCID 591683784-Chloro-6-(4-fluorophenyl)-2-(2-(S)-methylpyrrolidin-1-yl)pyrimidine

Product 1

HCID 591683424-[4-(5-Bromo-3-chloro-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(S)-methyl-pyrrolidin-1-yl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of 4-chloro-6-(4-fluoro-phenyl)-2-(2-(S)-methyl-pyrrolidin-1-yl)-pyrimidine (1.30 g, 4.44 mmol), 1-(5-bromo-3-chloro-pyridin-2-yl)-3-(R)-methyl-piperazine (1.2 g), and NaHCO3 (0.71 g, 8.46 mmol) in EtOH at 50° C. for 20 h. Concentrate under reduced pressure and partition between EtOAc and brine. Dry the organic layer (Na2SO4) and concentrate under reduced pressure. Purify the residue by flash column eluting with EtOAc-Hexanes (1:4) to afford the title compound as a white solid.

Workup

  1. temperatureHeat
  2. concentrationConcentrate under reduced pressure
  3. custompartition between EtOAc and brine
  4. dry with materialDry the organic layer (Na2SO4)
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash column
  7. washeluting with EtOAc-Hexanes (1:4)

Sources & evidence

ORD record
ord-876e6d46bc5d49829fdfd3961abbb1c9
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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