tert-Butyl piperazine-1-carboxylate → 4-[1,3-Bis(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1792058Notes

Reaction equation

HRID 1792058 reaction equation
Cl[C:2]1[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:9]2[C:8](=[O:16])[N:7]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C:6](=[O:25])[N:5]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:4]=2[N:3]=1.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].C12CCCCC1CCCNN=2>CN1CCCC1=O>[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][N:44]([C:2]2[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:9]3[C:8](=[O:16])[N:7]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:22])[CH3:23])[C:6](=[O:25])[N:5]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:4]=3[N:3]=2)[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 235368912,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl esterHCID 66879275Diazabicyclo[5.4.0]undecene

Product 1

HCID 235369414-[1,3-Bis(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl esterYield 45%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

2,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (470 mg) and 1-piperazinecarboxylic acid tert-butyl ester (218 mg) were dissolved in N-methylpyrrolidone (4 ml), and diazabicyclo[5.4.0]undecene (160 μl) was added to the solution. The mixture was stirred at 150° C. for 6.5 hours. The reaction mixture was filtered through Celite, diluted with chloroform, washed with water, and dried over anhydrous magnesium sulfate. After the solvent was removed by distillation from the organic layer, the residue was purified by silica gel column chromatography to give 277 mg of the title compound from the elution fraction of hexane-ethyl acetate (2:1)

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. additiondiluted with chloroform
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was removed by distillation from the organic layer
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-467d5e98194d49c9a3f7f03f8527eb1c
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

Loading…