Dimethylformamide → 4-chloro-3-iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 72704Notes

Reaction equation

HRID 72704 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2O)[N:4]([CH3:12])[N:3]=1.CN(C)C=O.P(Cl)(Cl)([Cl:20])=O.C(=O)(O)[O-].[Na+]>ClCCCl.CC(O)C.O>[Cl:20][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH3:12])[N:3]=[C:2]([I:1])[C:10]=12

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178481919HCID 178481919, compound

Product 1

HCID 867125614-chloro-3-iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

3-Iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-ol (C8) (9.35 g, 33.9 mmol), N,N-dimethylformamide (10.5 mL, 135 mmol) and phosphorus oxychloride (9.57 mL, 102 mmol) were combined in 1,2-dichloroethane (90 mL), and the mixture was heated to 80° C. for 2 hours. After cooling to room temperature, it was added portion-wise with vigorous stirring to a beaker containing a chilled mixture (0 to 5° C.) of sodium bicarbonate (28.7 g, 339 mmol) in 2-propanol (90 mL) and water (90 mL). The resulting mixture was stirred at 0 to 5° C. for 6 hours, and then concentrated in vacuo. The resulting solid was collected via filtration, and washed with water to provide the product as a yellow solid. Yield: 8.45 g, 28.7 mmol, 85%. 1H NMR (500 MHz, DMSO-d6) δ 4.04 (s, 3H), 8.82 (s, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionit was added portion-wise
  3. stirringThe resulting mixture was stirred at 0 to 5° C. for 6 hours
  4. concentrationconcentrated in vacuo
  5. filtrationThe resulting solid was collected via filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-93509582f6154dd6ad1ad2f7e80d4ef1
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Reaction notes

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