Acetone → HCID 178478397, compound

HRID 419725Notes

Reaction equation

HRID 419725 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[I:11]N1C(=O)CCC1=O.CN(C=O)C.CC(C)=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([I:11])[C:3]=12

Participants

6

Reactant 4

HCID 180AcetoneHCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178478397HCID 178478397, compoundYield 61.43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Charge 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (6.1 g, 1.0 eq), N-iodosuccinimide (NIS) (21.55 g, 2.0 eq) and DMF (213.5 mL) in a round bottom flask. Stir the reaction mass at 50° C. for 16 h. Monitor the reaction by TLC (10% acetone in DCM). Concentrate the reaction mass under reduced pressure. Charge ethyl acetate and wash with water and saturated aq. sodium chloride. Dry the organic layer over anhydrous sodium sulfate and concentrate the organic layer under reduced pressure to give 4-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (6.8 g, 61.43%).

Workup

  1. concentrationConcentrate the reaction mass under reduced pressure
  2. washCharge ethyl acetate and wash with water and saturated aq. sodium chloride
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. concentrationconcentrate the organic layer under reduced pressure

Sources & evidence

ORD record
ord-f2e27979dc644150a5f36d212d67cea4
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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