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

HRID 1444152
Notes
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Reaction equation

HRID 1444152 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:29])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[N:17]=[C:16](Cl)[N:15]=3)[C@H:10]([CH3:28])[CH2:9]2)=[N:6][CH:7]=1.Br.[CH3:31][C@@H:32]1[CH2:36][CH2:35][CH2:34][NH:33]1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:29])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[N:17]=[C:16]([N:33]4[CH2:34][CH2:35][CH2:36][C@H:32]4[CH3:31])[N:15]=3)[C@H:10]([CH3:28])[CH2:9]2)=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12444175(2R)-2-methylpyrrolidine hydrobromideHCID 591683034-[4-(5-Bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-2-chloro-6-(4-fluoro-phenyl)-pyrimidine

Product 1

HCID 591682874-[4-(5-bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent

Procedure

Heat a mixture of 4-[4-(5-bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-2-chloro-6-(4-fluoro-phenyl)-pyrimidine (7.7 g, 16.2 mmol), (R)-2-methylpyrrolidine hydrobromide [prepared essentially as described by Nijhuis et. al. (1989) J. Org. Chem. 54(1):209] (3.5 g, 21.1 mmol) and K2CO3 (5.1 g, 37.3 mmol) in DMA at 110° 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 10% EtOAc/hexanes. Concentrate under reduced pressure to give the title compound.

Workup

  1. temperatureHeat
  2. customprepared essentially
  3. customPartition the mixture between EtOAc and water
  4. dry with materialdry (Na2SO4) the organic layer
  5. concentrationconcentrate under reduced pressure
  6. customPurify with flash silica gel column
  7. washeluting with 10% EtOAc/hexanes
  8. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-f460629933d14d0b803622c7ca8a8e8b
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07662830B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes