Potassium Carbonate → HCID 24756930, compound

HRID 1890187Notes

Reaction equation

HRID 1890187 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][F:28]>O>[F:28][CH2:27][CH2:26][CH2:25][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 24864013HCID 24864013, compound

Product 1

HCID 24756930HCID 24756930, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

339 mg (corresponding to 1.0 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyrimidine that was sufficiently dried to remove moisture was dissolved in 20 mL of N,N-dimethylformamide, and 414 mg (corresponding to 3.0 mmol) of potassium carbonate was added thereto. The mixture was supplemented with 138 μL (corresponding to 1.5 mmol) of 1-bromo-3-fluoropropane, and then stirred at room temperature for 22 hours. After the completion of the reaction, the reaction solution was poured into water and extracted three times with chloroform. The combined chloroform layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was recrystallized from N,N-dimethylformamide to obtain 236 mg (corresponding to 0.594 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-iodoimidazo[1,2-a]pyrimidine (FIG. 1-8, Step 3).

Workup

  1. customto remove moisture
  2. dissolutionwas dissolved in 20 mL of N,N-dimethylformamide
  3. customAfter the completion of the reaction
  4. extractionextracted three times with chloroform
  5. washThe combined chloroform layer was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting crude product was recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-8b7b8461f473430da4a351ea16deec03
Source dataset
uspto-grants-2013_08
Patent number
US08506930B2

Reaction notes

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