Hydrochloric Acid → HCID 178462715, compound

HRID 408814Notes

Reaction equation

HRID 408814 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:10][C:11]2[C:16]([N:17]=1)=[C:15]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]1)[N:14]=[C:13]([CH3:26])[N:12]=2>CCOCC>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:10][C:11]2[C:16]([N:17]=1)=[C:15]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]1)[N:14]=[C:13]([CH3:26])[N:12]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178462714HCID 178462714, compound

Product 1

HCID 178462715HCID 178462715, compoundYield 199.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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. filtrationFilter the precipitate
  2. washwash with ether and DCM
  3. customDry under vacuum

Sources & evidence

ORD record
ord-a3659ff7746747fea090fff22047dd45
Source dataset
uspto-grants-2014_06
Patent number
US08759360B2

Reaction notes

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