Sodium Bicarbonate → 2-Chloro-4-(3-chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-pyrimidine

HRID 230943Notes

Reaction equation

HRID 230943 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])=[C:11]([Cl:16])[CH:10]=2)[N:3]=1.C(=O)(O)[O-].[Na+].[F:22][C:23]([F:37])([F:36])[C:24]1[C:25]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:26][CH:27]=[CH:28][CH:29]=1>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Cl:16])[CH:10]=2)[CH:5]=[C:6]([N:33]2[CH2:34][CH2:35][N:30]([C:25]3[C:24]([C:23]([F:37])([F:22])[F:36])=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:31][CH2:32]2)[N:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27777861-[3-(Trifluoromethyl)pyridin-2-yl]piperazineHCID 577610582,4-Dichloro-6-(3-chloro-4-fluoro-phenyl)-pyrimidine

Product 1

HCID 577614902-Chloro-4-(3-chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Combine 2,4-dichloro-6-(3-chloro-4-fluoro-phenyl)-pyrimidine (1.6 g, 5.75 mmol), sodium bicarbonate (1.28 g, 15 mmol), MeOH (100 mL) and cool over ice. Drip in a mixture of 1-(3-trifluoromethyl-pyridin-2-yl)-piperazine (1.33 g, 5.75 mmol) in MeOH (50 mL), and let the reaction stir for 16 hours at room temperature. Evaporate the mixture and purify directly using 10:1 hexanes/EtOAc, obtaining 2-chloro-4-(3-chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine as a white solid.

Workup

  1. customEvaporate the mixture
  2. custompurify directly

Sources & evidence

ORD record
ord-0b0dd860f44a40e78d051e086f470ed9
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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