Sodium Carbonate → 2,5-Dichloro-N-(5-(trifluoromethyl)-1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 536334Notes

Reaction equation

HRID 536334 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1[NH:7][N:6]=[C:5]([NH2:8])[CH:4]=1.[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([Cl:19])=[CH:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCO>[Cl:11][C:12]1[N:17]=[C:16]([NH:8][C:5]2[CH:4]=[C:3]([C:2]([F:10])([F:9])[F:1])[NH:7][N:6]=2)[C:15]([Cl:19])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 10340Sodium Carbonate2×HCID 2372592,4,5-Trichloropyrimidine2×HCID 196233053-(trifluoromethyl)-1H-pyrazol-5-amine

Product 1

HCID 866532692,5-Dichloro-N-(5-(trifluoromethyl)-1H-pyrazol-3-yl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(trifluoromethyl)-1H-pyrazol-3-amine (500 mg, 3.3 mmol), 2,4,5-trichloropyrimidine (607 mg, 3.3 mmol) and sodium carbonate (525 mg, 5 mmol) in anhydrous EtOH (10 mL) was stirred at rt. After one day, LCMS showed the reaction was not complete. Additional 2,4,5-trichloropyrimidine (0.15 mL) and sodium carbonate (525 mg) were added and the reaction continued for two more days. The solvent was evaporated, and the residue was extracted with DCM (3×20 mL). The combined DCM layers were washed with brine (10 mL), dried over Na2SO4 and evaporated. The crude product was purified by silica chromatography (0-50% EtOAc in hexanes gradient) to give 2,5-Dichloro-N-(5-(trifluoromethyl)-1H-pyrazol-3-yl)pyrimidin-4-amine as a light tan colored solid; ESMS m/z 297.9 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue was extracted with DCM (3×20 mL)
  3. washThe combined DCM layers were washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe crude product was purified by silica chromatography (0-50% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-bfd6b1f3ce584648a524eaac3f135221
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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