Triethylamine → HCID 178462714, compound

HRID 408813Notes

Reaction equation

HRID 408813 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[NH:6]2.[CH2:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH3:20].C(N(CC)CC)C>C(O)C>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:5]1[NH:6][C:7]2[C:3]([N:4]=1)=[C:2]([N:24]1[CH2:25][CH2:26][N:21]([CH2:19][CH3:20])[CH2:22][CH2:23]1)[N:10]=[C:9]([CH3:11])[N:8]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 791961-EthylpiperazineHCID 178432853HCID 178432853, compound

Product 1

HCID 178462714HCID 178462714, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a solution of 6-chloro-8-(2-chloro-phenyl)-2-methyl-9H-purine (0.5 g, 0.0017 mol), N-ethyl piperazine (0.22 g, 0.0019 mol), and triethyl amine (0.22 g, 0.0022 mol) in ethanol (10 mL) at 90° C. for 8 h. Alternatively, heat the reaction with microwave irradiation. Upon reaction completion, concentrate the reaction mixture under reduced pressure. Dissolve the residue in dry dichloromethane and wash with saturated sodium bicarbonate solution, water, and brine. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue on a silica gel column using MeOH:DCM (2:98) as eluent to give 8-(2-Chlorophenyl)-6-(4-ethylpiperazin-1-yl)-2-methyl-9H-purine (0.25 g). Add HCl (2 M solution in ethanol) (1.0 eq) into the mixture of 8-(2-chlorophenyl)-6-(4-ethylpiperazin-1-yl)-2-methyl-9H-purine (0.25 g, 0.0007 mol) in dry ether (2.5 mL) at 0° C. and stir for one hour at room temperature. Filter the precipitate, wash with ether and DCM. Dry under vacuum to give the title compound (0.275 g) as a white solid. ES/MS m/z 357 (M+1).

Workup

  1. temperatureAlternatively, heat
  2. customthe reaction
  3. customwith microwave irradiation
  4. customUpon reaction completion
  5. concentrationconcentrate the reaction mixture under reduced pressure
  6. dissolutionDissolve the residue in dry dichloromethane
  7. washwash with saturated sodium bicarbonate solution, water, and brine
  8. dry with materialDry the organic layer over anhydrous sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate under reduced pressure
  11. customto give a residue
  12. customPurify the residue on a silica gel column

Sources & evidence

ORD record
ord-5fecea4ddc8f46a5b42662adb183fce9
Source dataset
uspto-grants-2014_06
Patent number
US08759360B2

Reaction notes

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