Triethylamine → HCID 53386373, compound

HRID 2370066Notes

Reaction equation

HRID 2370066 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:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[N:6]2[CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15].[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(N(CC)CC)C>C(O)C>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:5]1[N:6]([CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:7]2[C:3]([N:4]=1)=[C:2]([N:29]1[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]1)[N:10]=[C:9]([CH3:11])[N:8]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 71762086HCID 71762086, compound

Product 1

HCID 53386373HCID 53386373, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a solution of 6-chloro-8-(2-chlorophenyl)-2-methyl-9-(2-methylsulfonylethyl)purine (0.3 g, 0.0007 mol), N-methylpiperazine (0.08 g, 0.0008 mol) and triethylamine (0.08 g, 0.0008 mol) in ethanol (15 mL) at 90° C. for 16 h. Cool and 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 to give a residue. Purify the residue on a silica gel column using dichloromethane:methanol (96:4) as eluent to afford a 8-(2-chlorophenyl)-6-(4-methylpiperazin-1-yl)-2-methyl-9-(2-methylsulfonylethyl)purine (0.24 g). ES/MS m/z 449 (M+1).

Workup

  1. temperatureCool
  2. concentrationconcentrate the reaction mixture under reduced pressure
  3. dissolutionDissolve the residue in dry dichloromethane
  4. washwash with saturated sodium bicarbonate solution, water, and brine
  5. dry with materialDry the organic layer over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give a residue
  9. customPurify the residue on a silica gel column

Sources & evidence

ORD record
ord-049abd2f03d041f8900f7e722aa188ce
Source dataset
uspto-grants-2014_04
Patent number
US08710063B2

Reaction notes

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