Potassium Iodide → HCID 21945997, compound

HRID 2216968Notes

Reaction equation

HRID 2216968 reaction equation
Br[CH:2]([C:5]1[C:6]([Cl:12])=[N:7][C:8]([Cl:11])=[N:9][CH:10]=1)[CH2:3][CH3:4].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[Cl:11][C:8]1[N:7]=[C:6]([Cl:12])[C:5]([CH:2]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[CH2:3][CH3:4])=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 21946016HCID 21946016, compound

Product 1

HCID 21945997HCID 21945997, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(±)-5-(1-Bromopropyl)-2,4-dichloro-pyrimidine (0.26 g; 0.96 mmol) (from Example 7b supra) was dissolved in acetonitrile (2.5 mL). p-Anisidine (0.12 g; 0.96 mmol) (Aldrich), potassium carbonate (0.15 g; 1.05 mmol) and potassium iodide (0.04 g; 0.24 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 40S, 15:85 to 20:80 ethyl acetate-hexanes gradient) gave crude (±)-[1-(2,4-dichloro-pyrimidin-5-yl)-propyl]-(4-methoxy-phenyl)-amine. (Yield 0.19 g; 64.3%). This material again showed 3 peaks for the pyrimidine ring proton in the same ratio as was seen in the starting material. This material was used without further purification.

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 40S, 15:85 to 20:80 ethyl acetate-hexanes gradient)

Sources & evidence

ORD record
ord-4ebcb7b8792f4b05a725a2e322b4fc49
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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