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

HRID 1792019Notes

Reaction equation

HRID 1792019 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22](CC3C=CC=CC=3)[C:21]3[C:20](=[O:30])[N:19]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:18](=[O:37])[N:17]([CH3:38])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[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:30])[N:19]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:18](=[O:37])[N:17]([CH3:38])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 235369644-[7-(Benzyl)-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 235369654-[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 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

4-[7-Benzyl-1-(ethoxycarbonylmethyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester was dissolved in acetic acid, and palladium hydroxide (ca. 10 mg) was added thereto. The reaction mixture was stirred at room temperature under hydrogen atmosphere overnight, filtered, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 111 mg of the title compound.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous solution of sodium bicarbonate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4374c8aae1004adb81c7f8b9ff4f53f8
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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