Phosphorus oxychloride → HCID 21104341, compound

HRID 1354297Notes

Reaction equation

HRID 1354297 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 oxychloride2×HCID 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. Removed excess phosphorous oxychloride under vacuum and added ice water to the residue. Extracted product with ethyl acetate, washed with 10% sodium carbonate, water, dried over sodium sulfate (anh) and removed solvent to give crude product. Crude product was chromatographed on silica gel column eluting with chloroform to give 1.10 g pure product (yield: 51%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. washExtracted product with ethyl acetate, washed with 10% sodium carbonate, water
  4. dry with materialdried over sodium sulfate (anh)
  5. customremoved solvent
  6. customto give crude product
  7. customCrude product was chromatographed on silica gel column
  8. washeluting with chloroform

Sources & evidence

ORD record
ord-7cd37d6720804bdcb12e66a2a328a9fd
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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