Phosphorus oxychloride → 4-chloro-1-(2,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1098200Notes

Reaction equation

HRID 1098200 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[N:14]1[C:18]2=[N:19][CH:20]=[N:21][C:22](O)=[C:17]2[CH:16]=[N:15]1>>[Cl:3][C:22]1[N:21]=[CH:20][N:19]=[C:18]2[N:14]([C:8]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]=3[CH3:6])[N:15]=[CH:16][C:17]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178425116HCID 178425116, compound

Product 1

HCID 431548064-chloro-1-(2,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidineYield 100.1%

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (7.76 mL, 83.24 mmol) was added to 1-(2,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (1 g, 4.16 mmol). The resulting solution was stirred at 100° C. for 2 hours. LCMS showed reaction was complete. The reaction mixture was evaporated. Ice/water and then EtOAc were added. The organic layer was separated and the aqueous layer re-extracted with EtOAc. The combined organics were washed with water, dried (MgSO4) and concentrated to give crude product (1.077 g, 100%) which was used without purification. 1H NMR (400 MHz, DMSO) δ 2.00 (3H, s), 2.35 (3H, s), 7.26-7.37 (3H, m), 8.72 (1H, s), 8.86 (1H, s); m/z (ES+) (M+H)+=259; HPLC tR=2.48 min.

Workup

  1. customreaction
  2. customThe reaction mixture was evaporated
  3. additionIce/water and then EtOAc were added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer re-extracted with EtOAc
  6. washThe combined organics were washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5f2bca2723ca47c2972d33091f5e8bc9
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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