2-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine → 2-(2-Amino-ethyl-amino)-9-ethyl-6-(3-fluor-phenyl-amino)-9H-purine hydrochloride

HRID 9909Notes

Reaction equation

HRID 9909 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[N:3]=1>C(N)CN.C(OCC)(=O)C>[ClH:1].[NH2:3][CH2:4][CH2:5][NH:6][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[N:3]=1

Participants

4

Reactant 1

HCID 219883192-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine

Product 1

HCID 219881882-(2-Amino-ethyl-amino)-9-ethyl-6-(3-fluor-phenyl-amino)-9H-purine hydrochloride

Reagents, catalysts & solvents 2

HCID 3301EthylenediamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.2 g (0.62 mmol) of 2-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine is stirred in 2.5 ml of ethylenediamine at 75° C. for 3 h, and the mixture is allowed to cool and is diluted with ethyl acetate. The organic phase is washed with water, separated off and dried over sodium sulfate. After removal of the solvent, the residue is dissolved in dioxane, and treated with 4 N HCl in dioxane. 2-(2-Amino-ethyl-amino)-9-ethyl-6-(3-fluor-phenyl-amino)-9H-purine hydrochloride is obtained as a crystalline precipitate by this procedure. This precipitate is filtered off and dried; m.p.>250° C.; FAB-MS: (M+H)+=315; Rf=0.6 (ethyl acetate:isopropanol:water:22% aqueous ammonium hydroxide solution=40:60:15:18).

Workup

  1. temperatureto cool
  2. washThe organic phase is washed with water
  3. customseparated off
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent
  6. dissolutionthe residue is dissolved in dioxane
  7. additiontreated with 4 N HCl in dioxane

Sources & evidence

ORD record
ord-91c9829968e24bb3a557a7a85a8195ae
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Reaction notes

Loading…