Potassium Iodide → (+/-)-[1-(2,4-Dichloro-pyrimidin-5-yl)-ethyl]-(4-methoxy-phenyl)-amine

HRID 1247638Notes

Reaction equation

HRID 1247638 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9](Br)[CH3:10])=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH3:10])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 21908975(+/-)-2,4-Dichloro-5-(1-bromoethyl)-pyrimidine

Product 1

HCID 10086026(+/-)-[1-(2,4-Dichloro-pyrimidin-5-yl)-ethyl]-(4-methoxy-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(±)-2,4-Dichloro-5-(1-bromoethyl)-pyrimidine (1.97 g; 7.70 mmol) (from Example 1c supra) was dissolved in acetonitrile (21 mL). p-Anisidine (0.95 g; 7.70 mmol) (Aldrich), potassium carbonate (1.17 g; 8.48 mmol) and potassium iodide (0.32 g; 1.93 mmol) were added and the mixture was stirred at room temperature. After 16 hours, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromatography (Biotage 40M, 20:80 to 25:75 ethyl acetate-hexanes gradient) gave (±)-[1-(2,4-dichloro-pyrimidin-5-yl)-ethyl]-(4-methoxy-phenyl)-amine. (Yield 1.82 g; 76.3%).

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (Biotage 40M, 20:80 to 25:75 ethyl acetate-hexanes gradient)

Sources & evidence

ORD record
ord-94082007b502404fad65d26aaae319ae
Source dataset
uspto-grants-2006_10
Patent number
US07129351B2

Reaction notes

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