Isopropyl iodide → 2-Chloro-N-(3-chlorophenyl)-9-isopropyl-9H-purin-6-amine

HRID 9898

Reaction equation

HRID 9898 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:25](I)([CH3:27])[CH3:26]>CN(C=O)C.O.O1CCOCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:25]([CH3:27])[CH3:26])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:3]=1

Participants

7

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 219882322-chloro-N-(3-chlorophenyl)-9H-purin-6-amine

Product 1

HCID 219882482-Chloro-N-(3-chlorophenyl)-9-isopropyl-9H-purin-6-amine

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

500 mg (1.78 mmol) of 2-chloro-6-(3-chloro-phenyl-amino)-purine are dissolved in a mixture of 29.5 ml of DMF/water (85/15) and 5 ml of dioxane by means of gentle heating. 870 mg (2.67 mmol) of caesium carbonate, followed by 1.78 ml (17.8 mmol) of isopropyl iodide are added at room temperature. The reaction mixture is stirred at room temperature for 18 hours. To bring the reaction to completion, the reaction mixture is stirred at 45° C. for a further 24 hours. When the reaction has ended, the reaction mixture is diluted with ethyl acetate, washed with water (2 times) and saturated sodium chloride solution and dried over magnesium sulfate. After filtration, the filtrate is concentrated under reduced pressure at 35° C. and the residue is dried under an HV. The resulting crude product is purified by crystallization from diethyl ether/hexane. 2-Chloro-6-(3-chloro-phenyl-amino)-9-isopropyl-9H-purine is obtained; Rf=0.46 (ethyl acetate); m.p. 128–129° C.

Workup

  1. additionare added at room temperature
  2. customthe reaction to completion
  3. stirringthe reaction mixture is stirred at 45° C. for a further 24 hours
  4. washwashed with water (2 times) and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated under reduced pressure at 35° C.
  8. customthe residue is dried under an HV
  9. customThe resulting crude product is purified by crystallization from diethyl ether/hexane

Sources & evidence

ORD record
ord-74fde67f2a9f47cb945db7fa6bea0160
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Linked notes

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