Sodium hydride → HCID 22347132, compound

HRID 898039Notes

Reaction equation

HRID 898039 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19]([N+]([O-])=O)[CH:18]=[CH:17][N:16]=1>CN(C)C=O>[Cl:14][C:15]1[CH:20]=[C:19]([N:4]2[C:5]3=[N:6][CH:7]=[N:8][C:9]([NH2:11])=[C:10]3[C:2]([I:1])=[N:3]2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridineHCID 178508725HCID 178508725, compound

Product 1

HCID 22347132HCID 22347132, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (4.12 g, 0.016 mol) in N,N-dimethylformamide (50 mL) was reacted with 60% sodium hydride in oil (0.75 g, 0.019 mol) at ambient temperature. The mixture was stirred for 15 minutes, and 2-chloro-4-nitropyridine (3.00 g, 0.019 mol) was added. The mixture was heated at 100° C. for 18 hours. The mixture was cooled to room temperature and the precipitate was filtered, washing with N,N-dimethylformamide (20 mL), and then slurried in ethyl acetate (50 mL) for four hours. The solid was filtered and dried in vacuo to give 1-(2-chloro-4-pyridyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.39 g, 0.009 mol) as a tan solid:

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe precipitate was filtered
  3. washwashing with N,N-dimethylformamide (20 mL)
  4. waitslurried in ethyl acetate (50 mL) for four hours
  5. filtrationThe solid was filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1f7674a1a27c45ba86d0f7e9acdceca3
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…