Potassium Carbonate → 4-[2-Chloro-6-(4-fluoro-phenyl)-pyrimidin-4-yl]-3-(R)-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 1444124Notes

Reaction equation

HRID 1444124 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.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][C@H:25]([CH3:29])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.O>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:6]2[CH:5]=[C:4]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[N:3]=[C:2]([Cl:1])[N:7]=2)[C@H:25]([CH3:29])[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2756811(R)-1-Boc-3-methylpiperazineHCID 116373222,4-Dichloro-6-(4-fluorophenyl)pyrimidine

Product 1

HCID 591683334-[2-Chloro-6-(4-fluoro-phenyl)-pyrimidin-4-yl]-3-(R)-methyl-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Heat a mixture of 2,4-dichloro-6-(4-fluoro-phenyl)-pyrimidine (2.8 g, 11.52 mmol), 3-(R)-methyl-piperazine-1-carboxylic acid tert-butyl ester (2.42 g, 12.1 mmol), and K2CO3 (3.2 g, 23.0 mmol) in DMA at 60° C. for 16 h. Dilute with water, extract with EtOAc, and wash with 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. extractionextract with EtOAc
  3. washwash with 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-af63d95531684ffba9dafdec963af964
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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