Phosphorus oxychloride → HCID 21104300, compound

HRID 1010832Notes

Reaction equation

HRID 1010832 reaction equation
[CH2:1]([N:5]1[C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[NH:12][C:13](=O)[C:8]=2[C:7]([CH3:22])=[N:6]1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:25])=O>>[CH2:1]([N:5]1[C:9]2=[N:10][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])=[N:12][C:13]([Cl:25])=[C:8]2[C:7]([CH3:22])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136008001HCID 136008001, compound

Product 1

HCID 21104300HCID 21104300, compoundYield 55%

Procedure

1-Butyl-6-(2-fluoro-phenyl)-3-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (1.23 g, 4.1 mmole) was dissolved in phosphorous oxychloride (15 ml) and heated to reflux overnight. The excess phosphorous oxychloride was removed under vacuum, the residue was treated with ice water, the product was extracted into ethyl acetate, washed with water, saturated sodium chloride, then dried over sodium sulfate (anh.) and the solvent was removed to give the crude product. The product was chromatographed on silica gel eluting with chloroform to give 723 mg of purified product (yield: 55%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe excess phosphorous oxychloride was removed under vacuum
  4. additionthe residue was treated with ice water
  5. extractionthe product was extracted into ethyl acetate
  6. washwashed with water, saturated sodium chloride
  7. dry with materialdried over sodium sulfate (anh.)
  8. customthe solvent was removed
  9. customto give the crude product
  10. customThe product was chromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-924fc7f83ee74ab384a105432dfee770
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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