Potassium Iodide → HCID 21946005, compound

HRID 2216981Notes

Reaction equation

HRID 2216981 reaction equation
Br[CH:2]([C:6]1[C:7]([Cl:13])=[N:8][C:9]([Cl:12])=[N:10][CH:11]=1)[CH:3]([CH3:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1>C(OCC)(=O)C>[Cl:12][C:9]1[N:8]=[C:7]([Cl:13])[C:6]([CH:2]([NH:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)[CH:3]([CH3:5])[CH3:4])=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 21946020HCID 21946020, compound

Product 1

HCID 21946005HCID 21946005, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(±)-5-(1-Bromo-2-methyl-propyl)-2,4-dichloro-pyrimidine (88.7 mg; 0.312 mmol) (from Example 11b supra) was combined with potassium carbonate (47.4 mg; 0.34 mmol), potassium iodide (14.9 mg; 0.09 mmol) and p-anisidine (38.7 mg; 0.31 mmol) (Aldrich) and stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with water and then brine. The organic phase with dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash chromatography (Biotage 12M; 10:90 to 30:70 ethyl acetate-hexanes gradient) gave (±)-[1-(2,4-dichloro-pyrimidin-5-yl)-2-methyl-propyl]-(4-methoxy-phenyl)-amine. (Yield 17.6 mg; 17.3%).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase with dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (Biotage 12M; 10:90 to 30:70 ethyl acetate-hexanes gradient)

Sources & evidence

ORD record
ord-76557c2a1bb24720934534411df84ad9
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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