N-Iodosuccinimide → HCID 178493476, compound

HRID 1778650Notes

Reaction equation

HRID 1778650 reaction equation
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[C:12]([Cl:20])[C:11]=1[C:21]1[N:26]=[C:25]2[NH:27][N:28]=[CH:29][C:24]2=[CH:23][N:22]=1>CN(C)C=O.O>[Cl:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[C:12]([Cl:20])[C:11]=1[C:21]1[N:26]=[C:25]2[NH:27][N:28]=[C:29]([I:1])[C:24]2=[CH:23][N:22]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 867228036-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178493476HCID 178493476, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

N-Iodosuccinimide (0.23 g, 1.0 mmol) was added to a solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine (0.30 g) in N,N-dimethylformamide (5.0 mL). The reaction mixture was stirred at 40° C. overnight. The reaction mixture was diluted with water and quenched with aqueous Na2S2O3. The precipitates formed were filtered, washed with water, ether, and dried in vacuum to afford the desired product (0.33 g). LCMS (M+H)+=450.8/452.8.

Workup

  1. customquenched with aqueous Na2S2O3
  2. customThe precipitates formed
  3. filtrationwere filtered
  4. washwashed with water, ether
  5. customdried in vacuum

Sources & evidence

ORD record
ord-ec9633839d0b4a10960612dc61716fcc
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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