Iodine → HCID 22599691, compound

HRID 1592222Notes

Reaction equation

HRID 1592222 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-05a86d397f7b45fb9566f73474748d9c
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

Loading…