Potassium Iodide → HCID 59586790, compound

HRID 2091937Notes

Reaction equation

HRID 2091937 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.[Cl:10][C:11]1[N:16]=[C:15](Cl)[C:14]([Cl:18])=[CH:13][N:12]=1.[I-].[K+]>CC(N(C)C)=O>[Cl:10][C:11]1[N:16]=[C:15]([NH:9][C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=2)[C:14]([Cl:18])=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 215072-Amino-4,6-dimethylpyridineHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 59586790HCID 59586790, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The mixture 4,6-dimethylpyridin-2-amine (61 mg, 0.50 mmol), 2,4,5-trichloropyrimidine (57 μL, 0.5 mmol), and potassium iodide (166 mg, 1.0 mmol) in 3 mL of DMA is heated at 90° C. overnight. The mixture is concentrated in vacuo and the resulting crude product is partitioned between EtOAc and brine. The collected organic extracts are dried (Na2SO4) and concentrated in vacuo to afford 2,5-dichloro-N-(4,6-dimethylpyridin-2-yl)pyrimidin-4-amine; ESMS m/z 269.0 (M+H+).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe resulting crude product is partitioned between EtOAc and brine
  3. dry with materialThe collected organic extracts are dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-381a025c35104141bfb1622571526574
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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