8-Oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide → 8-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 395890Notes

Reaction equation

HRID 395890 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=1[NH:16][C:17]([CH:19]1[CH2:25][CH:24]2[O:26][CH:21]([CH:22]=[CH:23]2)[CH2:20]1)=O>[OH-].[Na+].CO>[CH:21]12[O:26][CH:24]([CH:23]=[CH:22]1)[CH2:25][CH:19]([C:17]1[NH:16][C:3]3[C:4](=[O:15])[N:5]([CH2:12][CH2:13][CH3:14])[C:6](=[O:11])[N:7]([CH2:8][CH2:9][CH3:10])[C:2]=3[N:1]=1)[CH2:20]2

Participants

4

Reactant 1

HCID 865903668-Oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide

Product 1

HCID 102911968-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dioneYield 58.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 8-oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (0.185 mmol, 0.067 g) in 20% NaOH (1.23 ml) and MeOH (6.2 ml) was stirred and refluxed overnight. The reaction was cooled to room temperature and then concentrated to remove MeOH. The aqueous residue was extracted with Et2O and these extracts discarded. The aqueous was acidified (pH 2-3) with conc. HCl and then extracted with EtOAc. The combined EtOAc extracts were washed with H2O and brine and dried (MgSO4). Filtration and evaporation followed by flash column chromatography, eluting with 1:1 EtOAc/CH2Cl2, provided the title compound (0.037 g, 58%) as a beige solid. 1H NMR (300 MHz, CDCl3): 0.93-0.99 (m, 6H), 1.62-1.83 (m, 6H), 2.14-2.25 (m, 2H), 3.40-3.51 (m, 1H), 4.05-1.10 (m, 4H), 4.86 (br s, 2H), 6.25 (s, 2H).

Workup

  1. temperaturerefluxed overnight
  2. concentrationconcentrated
  3. customto remove MeOH
  4. extractionThe aqueous residue was extracted with Et2O
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc extracts were washed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and evaporation
  9. washeluting with 1:1 EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-b2d8ec3403824642b5ffb25fea4b2fab
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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