N,N-Dimethylaniline → 4-Chloro-3-methyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine

HRID 2046981Notes

Reaction equation

HRID 2046981 reaction equation
CN(C)C1C=CC=CC=1.O[C:11]1[N:16]=[C:15]([S:17][CH3:18])[N:14]=[C:13]2[NH:19][N:20]=[C:21]([CH3:22])[C:12]=12.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:11]1[N:16]=[C:15]([S:17][CH3:18])[N:14]=[C:13]2[NH:19][N:20]=[C:21]([CH3:22])[C:12]=12

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178503516HCID 178503516, compound

Product 1

HCID 1785034684-Chloro-3-methyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine

Procedure

To 40 mL of phosphorus oxychloride and 3 mL. of dimethylaniline is added 2.2 g of crude 4-hydroxy-3-methyl-6-methylmercaptopyrazolo[3,4-d]pyrimidine. The solution was refluxed for 30-60 minutes when all the solid had dissolved. The excess phosphorus was removed under reduced pressure. The residue was poured with vigorous stirring onto a mixture of ice water. After ten minutes, the aqueous solution was extracted with ether. The ether solution was washed with cold water and dried with anhydrous sodium sulfate. The product was obtained after filtering and removing ether under reduced pressure. 215.0 (M+1)+.

Workup

  1. temperatureThe solution was refluxed for 30-60 minutes when all the solid
  2. dissolutionhad dissolved
  3. customThe excess phosphorus was removed under reduced pressure
  4. additionThe residue was poured
  5. waitAfter ten minutes
  6. extractionthe aqueous solution was extracted with ether
  7. washThe ether solution was washed with cold water
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe product was obtained
  10. filtrationafter filtering
  11. customremoving ether under reduced pressure

Sources & evidence

ORD record
ord-ae1b6af8874c47dcb9a088a4653797f1
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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