Potassium Carbonate → 4-[4-(5-Bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-2-chloro-6-(4-fluoro-phenyl)-pyrimidine

HRID 1444151Notes

Reaction equation

HRID 1444151 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[N:3]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH3:30])[C:20]([N:23]2[CH2:28][CH2:27][NH:26][C@H:25]([CH3:29])[CH2:24]2)=[N:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Br:16][C:17]1[CH:18]=[C:19]([CH3:30])[C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:6]3[CH:5]=[C:4]([C:9]4[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=4)[N:3]=[C:2]([Cl:1])[N:7]=3)[C@H:25]([CH3:29])[CH2:24]2)=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 116373222,4-Dichloro-6-(4-fluorophenyl)pyrimidineHCID 574734721-(5-Bromo-3-methyl-pyridin-2-yl)-3-(R)-methyl-piperazine

Product 1

HCID 591683034-[4-(5-Bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-2-chloro-6-(4-fluoro-phenyl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Heat a mixture of 2,4-dichloro-6-(4-fluoro-phenyl)-pyrimidine (6.0 g, 24.7 mmol), 1-(5-bromo-3-methyl-pyridin-2-yl)-3-(R)-methyl-piperazine (7.0 g, 25.9 mmol) and K2CO3 (6.8 g, 49.4 mmol) in DMA at 60° C. for 16 h. Partition the mixture between EtOAc and water, dry (Na2SO4) the organic layer and concentrate under reduced pressure. Purify with flash silica gel column eluting with 15% EtOAc/hexanes. Concentrate under reduced pressure to give the title compound.

Workup

  1. temperatureHeat
  2. customPartition the mixture between EtOAc and water
  3. dry with materialdry (Na2SO4) the organic layer
  4. concentrationconcentrate under reduced pressure
  5. customPurify with flash silica gel column
  6. washeluting with 15% EtOAc/hexanes
  7. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-7d0b55b8e5e14960a23388495a0d6bc5
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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