Triethylamine → HCID 67426430, compound

HRID 888970Notes

Reaction equation

HRID 888970 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:10]2[C:15]([N:16]=1)=[C:14](Cl)[N:13]=[C:12]([CH3:18])[N:11]=2.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:10]2[C:15]([N:16]=1)=[C:14]([N:29]1[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]1)[N:13]=[C:12]([CH3:18])[N:11]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 59374559HCID 59374559, compound

Product 1

HCID 67426430HCID 67426430, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a solution of 8-(2-bromophenyl)-6-chloro-2-methyl-9-(tetrahydro-2H-pyran-4-yl)-9H-purine (0.0023 mol, 1.0 g), 1-methyl piperazine (0.0025 mol, 0.25 g, 1.1 equiv.) and triethylamine (0.0025 mol, 0.25 g, 1.1 equiv.) in ethanol (10.0 mL) at 90° C. for 16 h. Concentrate the reaction mixture under reduce 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 to give the residue. Purify the residue by silica gel chromatography eluting with dichloromethane:methanol 97:3 to give 8-(2-Bromo-phenyl)-2-methyl-6-(4-methyl-piperazin-1-yl)-9-(tetrahydro-pyran-4-yl)-9H-purine (0.71 g). Used as such for the next step.

Workup

  1. concentrationConcentrate the reaction mixture
  2. dissolutionDissolve the residue in dry dichloromethane
  3. washwash with saturated sodium bicarbonate solution, water, and brine
  4. dry with materialDry the organic layer over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customto give the residue
  8. customPurify the residue by silica gel chromatography
  9. washeluting with dichloromethane:methanol 97:3

Sources & evidence

ORD record
ord-7a57a16a9c4f46098eae2bdfebb15b9b
Source dataset
uspto-grants-2012_08
Patent number
US08252798B2

Reaction notes

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