Phosphorus oxychloride → HCID 23282763, compound

HRID 369846Notes

Reaction equation

HRID 369846 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:18][C:12]2[N:13]=[CH:14][N:15]=[C:16](O)[C:11]=2[CH:10]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:16]1[C:11]2[CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[NH:18][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178489269HCID 178489269, compound

Product 1

HCID 23282763HCID 23282763, compound

Procedure

Under argon, 6.2 g (25.7 mmol) of 6-(2-methoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol and 62 ml of phosphorus oxychloride are heated at 125° C. for 1.5 hours. The reaction mixture is poured into ice-water and extracted three times with ethyl acetate. The organic phases are washed with water, NaHCO3 solution and brine, dried with MgSO4 and concentrated by evaporation. Filtering through a silica gel column with ethyl acetate yields the title compound; TLC-Rf =0.8 (hexane/ethyl acetate [1:1]).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic phases are washed with water, NaHCO3 solution and brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated by evaporation
  5. filtrationFiltering through a silica gel column with ethyl acetate

Sources & evidence

ORD record
ord-d6a3fa7144aa493ab3133c2034f39486
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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