Phosphorus oxychloride → HCID 21104341, compound

HRID 1010828Notes

Reaction equation

HRID 1010828 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10](=O)[C:11]2[C:16]([CH3:17])=[N:15][N:14]([CH3:18])[C:12]=2[N:13]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:10]1[N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:13]=[C:12]2[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136008000HCID 136008000, compound

Product 1

HCID 21104341HCID 21104341, compoundYield 51%

Procedure

6-(2-Fluoro-phenyl)-1,3-dimethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (2.0 g, 7.74 mmole) was treated with 40 ml phosphorous oxychloride and heated to reflux overnight. The excess phosphorous oxychloride was removed under vacuum and ice water was added to the residue. The product was extracted with ethyl acetate, washed with 10% sodium carbonate, water, dried over sodium sulfate (anh) and the solvent was removed to give crude product. Crude product was chromatographed on silica gel column eluting with chloroform to give 1.10 g of pure product (yield: 51%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe excess phosphorous oxychloride was removed under vacuum and ice water
  4. additionwas added to the residue
  5. extractionThe product was extracted with ethyl acetate
  6. washwashed with 10% sodium carbonate, water
  7. dry with materialdried over sodium sulfate (anh)
  8. customthe solvent was removed
  9. customto give crude product
  10. customCrude product was chromatographed on silica gel column
  11. washeluting with chloroform

Sources & evidence

ORD record
ord-b8ea70571351437a813f036081da0b04
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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