Trifluoroacetic acid → 3-Methyl-8-piperazin-1-yl-7-prop-2-enylpurine-2,6-dione

HRID 1791995Notes

Reaction equation

HRID 1791995 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:29]([CH2:30][CH:31]=[CH2:32])[C:28]3[C:27](=[O:33])[NH:26][C:25](=[O:34])[N:24]([CH3:35])[C:23]=3[N:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH2:30]([N:29]1[C:28]2[C:27](=[O:33])[NH:26][C:25](=[O:34])[N:24]([CH3:35])[C:23]=2[N:22]=[C:21]1[N:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1)[CH:31]=[CH2:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 235369544-(7-Allyl-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 6774233-Methyl-8-piperazin-1-yl-7-prop-2-enylpurine-2,6-dioneYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (294 μl) was added dropwise to a solution of 4-(7-allyl-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester (150 mg) in methylene chloride (2 ml), and the reaction mixture was stirred at room temperature for 1 hour and 30 minutes. The solvent was removed by distillation at reduced pressure from the reaction mixture. The residue was subjected to azeotropic distillation with toluene, and then was purified by silica gel column chromatography to give 85 mg of the title compound from a fraction eluted with methanol-ethyl acetate (1:10).

Workup

  1. customThe solvent was removed by distillation at reduced pressure from the reaction mixture
  2. distillationThe residue was subjected to azeotropic distillation with toluene
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-af7ad205287341fbbed303d22e378a13
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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