Phosphorus oxychloride → HCID 10545846, compound

HRID 1602281Notes

Reaction equation

HRID 1602281 reaction equation
[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16](O)=[C:11]2[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:28])=O>>[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16]([Cl:28])=[C:11]2[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178489914HCID 178489914, compound

Product 1

HCID 10545846HCID 10545846, compound

Procedure

A mixture of 2.48 g (7.46 mmol) of 1-benzyl-4-hydroxy-3-(3-methoxy-phenyl)-pyrazolo[3,4-d]pyrimidine and 30 ml of phosphorus oxychloride is heated under reflux for 10 hours and then, with stirring, poured slowly into ice-water. The reaction mixture is stirred for a further 2 hours at 0-10° C. and filtered and the filter residue is washed with water. The crude product is dissolved in methylene chloride and the organic phase is washed with brine, dried over sodium sulfate and concentrated by evaporation in vacuo. Purification of the residue by flash chromatography on silica gel (230-400 mesh) using methylene chloride and methylene chloride/methanol mixtures (99:1 and 49:1) yields the title compound; m.p. 99-101° C.; FAB-MS: (M+H)+ =351.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 10 hours
  3. stirringThe reaction mixture is stirred for a further 2 hours at 0-10° C.
  4. filtrationfiltered
  5. washthe filter residue is washed with water
  6. dissolutionThe crude product is dissolved in methylene chloride
  7. washthe organic phase is washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated by evaporation in vacuo
  10. customPurification of the residue by flash chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-60e82492ad30435ab0e2466aae51daf6
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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