Sodium Bicarbonate → 5-Chloro-6-{4-[2-chloro-6-(4-fluoro-phenyl)-pyrimidin-4-yl]piperazin-1-yl}-nicotinic acid ethyl ester

HRID 1444102Notes

Reaction equation

HRID 1444102 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([O-])(O)=O.[Na+].[CH2:21]([O:23][C:24](=[O:38])[C:25]1[CH:30]=[C:29]([Cl:31])[C:28]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[N:27][CH:26]=1)[CH3:22]>CCO>[CH2:21]([O:23][C:24](=[O:38])[C:25]1[CH:30]=[C:29]([Cl:31])[C:28]([N:32]2[CH2:37][CH2:36][N:35]([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)[CH2:34][CH2:33]2)=[N:27][CH:26]=1)[CH3:22]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 116373222,4-Dichloro-6-(4-fluorophenyl)pyrimidineHCID 22028944Ethyl 5-chloro-6-(piperazin-1-YL)nicotinate

Product 1

HCID 591683325-Chloro-6-{4-[2-chloro-6-(4-fluoro-phenyl)-pyrimidin-4-yl]piperazin-1-yl}-nicotinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2,4-dichloro-6-(4-fluoro-phenyl)-pyrimidine (2.82 g, 0.12 mol) and NaHCO3 (1.95 g, 0.023 mol) in EtOH at 0° C., add 5-chloro-6-piperazin-1-yl-nicotinic acid ethyl ester (3.44 g, 0.013 mol). Remove the ice bath and stir at room temperature for 16 h. Concentrate under reduced pressure and partition between EtOAc and brine. Dry the organic layer (Na2SO4) and concentrate under reduced pressure to give the title compound.

Workup

  1. customRemove the ice bath
  2. concentrationConcentrate under reduced pressure
  3. custompartition between EtOAc and brine
  4. dry with materialDry the organic layer (Na2SO4)
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-563e5b1ee36541839db83f63b65e932d
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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