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

HRID 2195035Notes

Reaction equation

HRID 2195035 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-86cf8fb29b3f47039da3e8e9eeb4645b
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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