Phosphorus oxychloride → HCID 23291364, compound

HRID 1586033Notes

Reaction equation

HRID 1586033 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12](O)[C:11]=1[I:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:20])=O>>[CH2:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]([Cl:20])[C:11]=1[I:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518152HCID 178518152, compound

Product 1

HCID 23291364HCID 23291364, compoundYield 97%

Procedure

A solution of 6-benzyloxymethyl-4-hydroxy-5-iodo-pyrimidine (6.56 g, 1.9 mmol) dissolved in phosphorus oxychloride (200 ml) was stirred at reflux for 20 min. The POCl3 was removed under reduced pressure and the residue evaporated from toluene. The reddish residue was partitioned between ice-water and t-butyl methyl ether, then treated with NaHCO3, and the layers separated, and the aqueous layer was further extracted (×2). The combined organic extracts were washed twice with 5% sodium bicarbonate solution and once with brine, and then dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product as a brown oil (6.64 g, 97%).

Workup

  1. temperatureat reflux for 20 min
  2. customThe POCl3 was removed under reduced pressure
  3. customthe residue evaporated from toluene
  4. customThe reddish residue was partitioned between ice-water and t-butyl methyl ether
  5. additiontreated with NaHCO3
  6. customthe layers separated
  7. extractionthe aqueous layer was further extracted (×2)
  8. washThe combined organic extracts were washed twice with 5% sodium bicarbonate solution and once with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a4484651acf47faa360c5f435a34fd7
Source dataset
uspto-grants-1999_08
Patent number
US05942516

Reaction notes

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