Potassium Carbonate → (2,4-Dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amine

HRID 1243222Notes

Reaction equation

HRID 1243222 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9]I)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[CH3:18]>CC(C)=O.O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9][NH:23][C:22]2[CH:24]=[CH:25][C:19]([CH2:17][CH3:18])=[CH:20][CH:21]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 115044-EthylanilineHCID 219393522,4-Dichloro-5-(iodomethyl)pyrimidine

Product 1

HCID 11426039(2,4-Dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A heterogeneous mixture of 2,4-dichloro-5-(iodomethyl)pyrimidine (31.07 g, 107.3 mmol) (from Example 1c supra) and potassium carbonate (74 g, 536.5 mmol) in acetone (535 mL) was treated with 4-ethylaniline (13.3 mL, 107.3 mmol) (Aldrich). The mixture was stirred at room temperature overnight, then diluted with water (500 mL) and extracted with ethyl acetate. The combined organic layers were successively washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine, then dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure. The crude mixture was purified by flash chromatography (20% ethyl acetate in hexanes) to give (2,4-dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amine as a beige solid. (Yield 21.4 g, 70%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were successively washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture was purified by flash chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-09493f959b2a4f5b8a7cb16468cf836b
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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