Ethylenediamine → 2-(2-Amino-ethyl-amino)-6-(3-chloro-phenylamino)-9-ethyl-9H-purine

HRID 9894Notes

Reaction equation

HRID 9894 reaction equation
Cl[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]([Cl:20])[CH:15]=2)[N:3]=1.[CH2:21]([NH2:24])[CH2:22][NH2:23]>C(OCC)(=O)C>[NH2:23][CH2:22][CH2:21][NH:24][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]([Cl:20])[CH:15]=2)[N:3]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 110013202-Chloro-n-(3-chlorophenyl)-9-ethyl-9h-purin-6-amine

Product 1

HCID 99494482-(2-Amino-ethyl-amino)-6-(3-chloro-phenylamino)-9-ethyl-9H-purine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

250 mg (0.81 mmol) of 2-chloro-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine are dissolved in 5.8 ml (97 mmol) of ethylenediamine and the solution is heated under reflux for 3 hours (oil bath temperature of 150° C.). After cooling to room temperature, the reaction mixture is taken up in ethyl acetate (250 ml) and extracted with water (150 ml). The aqueous phase is extracted twice with ethyl acetate and the combined organic extracts are washed successively with saturated sodium bicarbonate solution, water 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 crude product is recrystallized from diethyl ether. 2-(2-Amino-ethyl-amino)-6-(3-chloro-phenylamino)-9-ethyl-9H-purine is obtained; Rf=0.22 (methylene chloride:methanol:concentrated aqueous ammonium hydroxide solution=900:100:1); FAB-MS: (M+H)+=322; m.p. 79–80° C.

Workup

  1. temperaturethe solution is heated
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with water (150 ml)
  4. extractionThe aqueous phase is extracted twice with ethyl acetate
  5. washthe combined organic extracts are washed successively with saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate is concentrated under reduced pressure at 35° C.
  9. customthe residue is dried under an HV
  10. customThe crude product is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-0e289eb070e44fd5bd336895d77677ad
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Reaction notes

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