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

HRID 536326Notes

Reaction equation

HRID 536326 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH3:13][C:14]1[NH:18][N:17]=[C:16]([NH2:19])[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:19][C:16]2[CH:15]=[C:14]([CH3:13])[NH:18][N:17]=2)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 582551692-chloro-N-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-dichloro-5-(trifluoromethyl)pyrimidine (1.06 g, 4.86 mmol), 5-methyl-1H-pyrazol-3-amine (472.2 mg, 4.86 mmol) and sodium carbonate (2.06 g, 19.4 mmol) in 100 mL of EtOH was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo. The crude solid was partitioned between EtOAc and water. The combined organic extracts were dried (Na2SO4), concentrated in vacuo, and purified by silica chromatography (EtOAc/hexanes: 1/1) to afford 2-chloro-N-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidin-4-amine; ESMS m/z 278.0 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude solid was partitioned between EtOAc and water
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by silica chromatography (EtOAc/hexanes: 1/1)

Sources & evidence

ORD record
ord-aa3c9f49e9dc4a588fe3c064e9521696
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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