Pyridine → HCID 23081908, compound

HRID 1792024Notes

Reaction equation

HRID 1792024 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:22][C:21]3[C:20](=[O:23])[N:19]([CH3:24])[C:18](=[O:25])[N:17]([CH3:26])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)=[O:28].N1C=CC=CC=1>O1CCCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:22]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH:27]=[O:28])[C:21]3[C:20](=[O:23])[N:19]([CH3:24])[C:18](=[O:25])[N:17]([CH3:26])[C:16]=3[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 2921892-Formylphenylboronic acidHCID 23081921HCID 23081921, compound

Product 1

HCID 23081908HCID 23081908, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(1,3-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester (226 mg), 2-formylphenyl boronic acid (200 mg), and copper (II) acetate (200 mg) were suspended in anhydrous tetrahydrofuran (5 ml), and pyridine (0.2 ml) was added thereto. The reaction mixture was stirred at room temperature for 5 days, filtered through a short column filled with silica gel, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain 51 mg of the title compound from a fraction eluted with hexane-ethyl acetate (1:1).

Workup

  1. filtrationfiltered through a short column
  2. additionfilled with silica gel
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-de5ab057cc874dc8a359fec67745cd09
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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