Triethylamine → HCID 67425498, compound

HRID 888972Notes

Reaction equation

HRID 888972 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:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])[N:6]2[CH:12]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1.[CH2:30]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[CH3:31].C(N(CC)CC)C>C(O)C>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:5]1[N:6]([CH:12]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15]2)[C:7]2[C:3]([N:4]=1)=[C:2]([N:35]1[CH2:36][CH2:37][N:32]([CH2:30][CH3:31])[CH2:33][CH2:34]1)[N:10]=[C:9]([CH3:11])[N:8]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 791961-EthylpiperazineHCID 59374585HCID 59374585, compound

Product 1

HCID 67425498HCID 67425498, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a solution of tert-butyl 3-(6-chloro-8-(2-chlorophenyl)-2-methyl-9H-purin-9-yl)azetidine-1-carboxylate (0.012 mol, 5.5 g), N-ethyl piperazine (0.013 mol, 1.59 g, 1.1 equiv.), and triethylamine (0.013 mol, 1.41 g, 1.1 equiv.) in ethanol (25.0 mL) at 90° C. for 16 hours. Concentrate the reaction mixture under reduced pressure. Dissolve the residue in dry dichloromethane. 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 the residue. Purify the residue by silica gel chromatography eluting with dichloromethane:methanol 98:2 to give tert-butyl 3-(8-(2-chlorophenyl)-6-(4-ethylpiperazin-1-yl)-2-methyl-9H-purin-9-yl)azetidine-1-carboxylate (3.0 g). MS (m/z): 512.31 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  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 under reduced pressure
  7. customto give the residue
  8. customPurify the residue by silica gel chromatography
  9. washeluting with dichloromethane:methanol 98:2

Sources & evidence

ORD record
ord-8ccf2fe9b4f8475ab1f05002aff7a0b1
Source dataset
uspto-grants-2012_08
Patent number
US08252798B2

Reaction notes

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