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

HRID 1792017Notes

Reaction equation

HRID 1792017 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[N:10]=[C:9]1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(OCC)(=O)C>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:9]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]3[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH3:19])[C:11]=3[N:10]=2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 9115837-benzyl-8-chloro-3-methyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 235369514-(7-Benzyl-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl esterYield 96.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7-Benzyl-8-chloro-3-methyl-3,7-dihydropurine-2,6-dione (130 mg) and 1-piperazine carboxylic acid tert-butyl ester (250 mg) were stirred at 150° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, and the resulting suspension was filtered to give white solid. This solid was purified by silica gel column chromatography to obtain 190 mg of the title compound from a fraction eluted with ethyl acetate.

Workup

  1. filtrationthe resulting suspension was filtered
  2. customto give white solid
  3. customThis solid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bae984a2d7ad483fb5f6c32628af5994
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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