Pyridine → 4-[7-(2-Methoxyphenyl)-1-(ethoxycarbonylmethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1792020Notes

Reaction equation

HRID 1792020 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]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:18](=[O:30])[N:17]([CH3:31])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1B(O)O.N1C=CC=CC=1>O1CCCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[O:33][CH3:32])[C:21]3[C:20](=[O:23])[N:19]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:18](=[O:30])[N:17]([CH3:31])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27339582-Methoxyphenylboronic acidHCID 235369654-[1-(Ethoxycarbonylmethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 235369634-[7-(2-Methoxyphenyl)-1-(ethoxycarbonylmethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-[1-(Ethoxycarbonylmethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester, 2-methoxyphenyl boronic acid (60 mg), and copper (II) acetate (200 mg) were dissolved in anhydrous tetrahydrofuran (5 ml), and pyridine (0.2 ml) was added thereto. The reaction mixture was stirred at room temperature for 3 days, filtered through a short column packed with NH-silica gel, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain 18 mg of the title compound from a fraction eluted with hexane-ethyl acetate (1:1).

Workup

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

Sources & evidence

ORD record
ord-afa96f505db54a0193b7dfd6f420b2c1
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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