Methyl iodide → N-(2-Chloro-4-pyrimidinyl)-N,2,3-trimethyl-2H-indazol-6-amine

HRID 1801850Notes

Reaction equation

HRID 1801850 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[C:16]([CH:17]=2)=[N:15][N:14]([CH3:18])[C:13]=3[CH3:19])[CH:5]=[CH:4][N:3]=1.[C:20](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:20])[C:9]2[CH:10]=[CH:11][C:12]3[C:16]([CH:17]=2)=[N:15][N:14]([CH3:18])[C:13]=3[CH3:19])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11637631N-(2-Chloro-4-pyrimidinyl)-2,3-dimethyl-2H-indazol-6-amine

Product 1

HCID 11608962N-(2-Chloro-4-pyrimidinyl)-N,2,3-trimethyl-2H-indazol-6-amineYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine (2.21 g; 8 mmol, 1 equiv) was dissolved in DMF (11 ml) and cesium carbonate (7.9 g; 24.2 mmol, 3 equiv) was added. The reaction mixture was stirred for 30 min under nitrogen. Iodomethane (0.8 ml, 13 mmol, 1.6 equiv) was added and the reaction mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured in ice cold water and stirred for 30 minutes. The resulting precipitate was collected by filtration to yield the desired compound (0.84 g, 37%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 hrs
  2. additionThe reaction mixture was poured in ice cold water
  3. stirringstirred for 30 minutes
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-2a481b647c3c45d780f7e2948ea83963
Source dataset
uspto-grants-2013_01
Patent number
US08349861B2

Reaction notes

Loading…