Iodine → HCID 22599691, compound

HRID 1759944Notes

Reaction equation

HRID 1759944 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=[CH:7][N:6]=1)[C:2]#[CH:3].[OH-].[Na+].[I:20]I>C(O)C>[I:20][C:3]#[C:2][CH2:1][O:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 22599760HCID 22599760, compound

Product 1

HCID 22599691HCID 22599691, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.3 g of 4-(2-propynyloxy)-6-phenoxypyrimidine dissolved in 3 ml of ethanol were added 1.87 ml of 10% sodium hydroxide and 0.51 g of iodine at 0° C. The mixture was stirred at room temperature for 5 hours, and the alcohol was distilled out under reduced pressure. A saturated sodium thiosulfate solution was added to the residue, which was extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.12 g of 4-(3-iodo-2-propynyloxy)-6-phenoxypyrimidine (the present compound (171)).

Workup

  1. distillationthe alcohol was distilled out under reduced pressure
  2. additionA saturated sodium thiosulfate solution was added to the residue, which
  3. extractionwas extracted three times with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-942fe886b9bb42b2b7e8324e287b4a72
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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