Phosphorus oxychloride → HCID 178434472, compound

HRID 2426104Notes

Reaction equation

HRID 2426104 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][C:5]2[C:10]=1[C:9](=O)[N:8]=[CH:7][N:6]=2.C(N(C(C)C)CC)(C)C.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[NH:4][N:3]=[C:2]([CH3:1])[C:10]=12

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 536298293-Methyl-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 178434472HCID 178434472, compound

Procedure

To a stirred suspension of 3-methyl-pyrazolo[3,4-d]pyrimidin-4-one (7.50 g, 50.0 mmol, Example 2) in phosphorus oxychloride (150 mL) was added diisopropylethylamine (31 mL, 175 mmol, Aldrich). The mixture was heated at reflux for 2.5 hours before the solvent was evaporated under reduced pressure. The residue was treated with ice (200 g) and made slightly basic with 4N aqueous sodium hydroxide solution and extracted with ethyl acetate (3×250 mL). The combined organic extracts were washed with water, brine, dried and concentrated to give 4-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine as a white solid. (Yield 6.38 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2.5 hours before the solvent
  3. customwas evaporated under reduced pressure
  4. additionThe residue was treated with ice (200 g)
  5. extractionextracted with ethyl acetate (3×250 mL)
  6. washThe combined organic extracts were washed with water, brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-72a0ea1cac81476683bb0a59f1c84677
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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