Reaction #742296

Reaction equation

Phosphorus oxychloride

1-(2,6-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol

→

product

Yield 87.0%

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

Yield 87.0%

Conditions

Workup

1. 1
   Otherreaction
2. 2
   OtherThe reaction mixture was evaporated
3. 3
   workup.ADDITIONIce/water and then EtOAc were added
4. 4
   OtherThe organic layer to was separated
5. 5
   Extractionthe aqueous layer re-extracted with EtOAc
6. 6
   WashThe combined organics were washed with water
7. 7
   Dryingdried (MgSO4)
8. 8
   Concentrationconcentrated

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.

Source