Phosphorus oxychloride → HCID 15521236, compound

HRID 324379Notes

Reaction equation

HRID 324379 reaction equation
[CH3:1][S:2][C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:13])=[N:9][C:10]=2O)[N:5]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=2[Cl:22])[N:4]=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:10]1[N:9]=[C:8]([CH3:13])[N:7]=[C:6]2[N:5]([C:14]3[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=3[Cl:22])[N:4]=[C:3]([S:2][CH3:1])[C:11]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178503609HCID 178503609, compound

Product 1

HCID 15521236HCID 15521236, compoundYield 96%

Procedure

A mixture of 3-methylsulfanyl-6-methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-4-ol (3.700 g, 9.85 mmol) and phosphorous oxychloride (18.115 g, 11 ml) was heated at reflux for 4 hours. The mixture was cooled and poured over ice-water and stirred for 10 minutes. Precipitate formed and was filtered to give a brown solid. The brown solid was pumped in vacuo to give 3.718 g (96% yield). 1H NMR (CDCl3): 2.65(s,3H),2.7(s,3H), 7.5(s,2H)ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. customPrecipitate formed
  5. filtrationwas filtered
  6. customto give a brown solid
  7. customto give 3.718 g (96% yield)

Sources & evidence

ORD record
ord-c0f97a95781749999c61ebebb2a822ad
Source dataset
uspto-grants-2001_04
Patent number
US06218397B1

Reaction notes

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