Phosphorus oxychloride → 4-chloro-1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1093185Notes

Reaction equation

HRID 1093185 reaction equation
[CH:1]([N:4]1[C:8]2=[N:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[N:11][C:12](O)=[C:7]2[CH:6]=[N:5]1)([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:12]1[N:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[N:9]=[C:8]2[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][C:7]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1784566311-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol

Product 1

HCID 866293704-chloro-1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidineYield 100%

Procedure

A suspension of 1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (0.76 g, 2.5 mmol) in phosphorus oxychloride (20 mL) was heated a sealed tube with a heat gun until all of the starting material was dissolved. After allowing the mixture to cool to room temperature it was concentrated to dryness under reduced pressure, leaving a pale yellow solid which was then triturated with water and collected by Buchner filtration. The solid was further washed with water and dried under house vacuum to provide 4-chloro-1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidine (0.90 g, >100%) as a pale yellow solid. MS (ES+): 317.7, 319.8 (M+H)+

Workup

  1. temperaturewas heated a sealed tube with a heat gun until all of the starting material
  2. dissolutionwas dissolved
  3. concentrationwas concentrated to dryness under reduced pressure
  4. customleaving a pale yellow solid which
  5. customwas then triturated with water
  6. filtrationcollected by Buchner filtration
  7. washThe solid was further washed with water
  8. customdried under house vacuum

Sources & evidence

ORD record
ord-104a55c1190f4354ac2c773e2f52e3bf
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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