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

HRID 9914Notes

Reaction equation

HRID 9914 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]([C:20]#[N:21])[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]([C:20]#[N:21])[CH:15]=2)[N:3]=1

Participants

4

Reactant 1

HCID 219882732-chloro-9-ethyl-6-(3-cyano-phenyl-amino)-9H-purine

Product 1

HCID 219881842-(2-Amino-ethyl-amino)-6-(3-cyano-phenyl-amino)-9-ethyl-9H-purine hydrochloride

Reagents, catalysts & solvents 2

HCID 3301EthylenediamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.2 g (0.6 mmol) of 2-chloro-9-ethyl-6-(3-cyano-phenyl-amino)-9H-purine is stirred in 2.5 ml of ethylenediamine at 75° C. for 3.5 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 3 ml of dioxane and treated with 4 N HCl in dioxane. 2-(2-Amino-ethyl-amino)-6-(3-cyano-phenyl-amino)-9-ethyl-9H-purine hydrochloride is obtained as a crystalline precipitate. This is filtered off and dried; m.p. 200° C.; FAB-MS: (M+H)+=323; Rf=0.5 (ethyl acetate:i-propanol:water: 22% aqueous ammonium hydroxide solution=40:60:15:10).

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 3 ml of dioxane
  7. additiontreated with 4 N HCl in dioxane

Sources & evidence

ORD record
ord-a04becea6d8048c8891d2c8f7011ff40
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Reaction notes

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