Ethylenediamine → 2-(2-Amino-ethylamino)-6-(3-chloro-phenyl-amino)-9-isopropyl-9H-purine

HRID 9897

Reaction equation

HRID 9897 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[N:3]=1.[CH2:22]([NH2:25])[CH2:23][NH2:24]>C(OCC)(=O)C>[NH2:24][CH2:23][CH2:22][NH:25][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[N:3]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 219882482-Chloro-N-(3-chlorophenyl)-9-isopropyl-9H-purin-6-amine

Product 1

HCID 219882262-(2-Amino-ethylamino)-6-(3-chloro-phenyl-amino)-9-isopropyl-9H-purine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

200 mg (0.58 mmol) of 2-chloro-6-(3-chloro-phenyl-amino)-9-isopropyl-9H-purine are dissolved in 6 ml (90 mmol) of ethylenediamine and the mixture 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 250 ml of ethyl acetate and extracted with 150 ml of water. The aqueous phase is extracted twice with ethyl acetate and the combined organic extracts are washed 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 dried under an HV. 2-(2-Amino-ethylamino)-6-(3-chloro-phenyl-amino)-9-isopropyl-9H-purine is obtained; Rf=0.27 (methylene chloride:methanol:concentrated ammonium hydroxide solution=900:100:1); EI-MS: (M+H)+=346; m.p. 55–56° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with 150 ml of water
  4. extractionThe aqueous phase is extracted twice with ethyl acetate
  5. washthe combined organic extracts are washed 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. customdried under an HV

Sources & evidence

ORD record
ord-10cbb19efc2447da90278f6f11f5b438
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Linked notes

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