Phosphorus oxychloride → 4-chloro-1-(2,6-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 655114Notes

Reaction equation

HRID 655114 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[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[C:7]([Cl:6])=[CH:12][CH:11]=[CH:10][C:9]=3[Cl:13])[N:15]=[CH:16][C:17]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517921HCID 178517921, compound

Product 1

HCID 574386694-chloro-1-(2,6-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidineYield 87%

Procedure

Phosphorus oxychloride (7.96 mL, 85.38 mmol) was added to 1-(2,6-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate BA4) (1.2 g, 4.27 mmol). The resulting solution was stiffed at 100° C. for 20 hours. LCMS showed reaction was complete. The reaction mixture was evaporated. Ice/water and then EtOAc were added. The organic layer to was separated and the aqueous layer re-extracted with EtOAc. The combined organics were washed with water, dried (MgSO4) and concentrated to give the product (1.110 g, 87%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.46-7.58 (3H, m), 8.45 (1H, s), 8.82 (1H, s); m/z (ES+) (M+H)+=299; HPLC tR=2.77 min.

Workup

  1. customreaction
  2. customThe reaction mixture was evaporated
  3. additionIce/water and then EtOAc were added
  4. customThe organic layer to 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-2927e481e0ba486fbb770339a97793d5
Source dataset
uspto-grants-2011_12
Patent number
US08071585B2

Reaction notes

Loading…