Potassium Carbonate → [(2,4-Dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amine

HRID 1243181Notes

Reaction equation

HRID 1243181 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9]Cl)=[CH:4][N:3]=1.F[C:12]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:13]=1[NH2:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9][NH:14][C:13]2[CH:12]=[CH:18][C:17]([O:19][CH3:20])=[CH:16][CH:15]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 37563832-Fluoro-4-methoxyanilineHCID 135682792,4-Dichloro-5-(chloromethyl)pyrimidine

Product 1

HCID 21939303[(2,4-Dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,4-dichloro-5-chloromethyl-pyrimidine (3.70 g, 18.7 mmol) (from Example 1b supra), 2-fluoro-4-methoxy-phenylamine (2.40 g, 17.0 mmol) (from Example 14a supra) and potassium carbonate (4.70 g, 34.0 mmol) in acetone (100 mL) was stirred at room temperature for 18 hours. The precipitate was filtered off and the solution was concentrated under reduced pressure. The residue was diluted with ethyl acetate and washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. This residue was purified by flash chromatography eluting with ethyl acetate-hexanes (1:4) to give [(2,4-dichloropyrimidin-5-yl)methyl]-(4-methoxyphenyl)-amine. (Yield 3.99 g, 78%).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe solution was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThis residue was purified by flash chromatography
  9. washeluting with ethyl acetate-hexanes (1:4)

Sources & evidence

ORD record
ord-aee47a38195744a099f750d70709e0e1
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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