Cyclohexene → HCID 178450472, compound

HRID 2372325Notes

Reaction equation

HRID 2372325 reaction equation
[CH2:1]([O:5][CH2:6][CH:7]([O:17][CH2:18][N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([NH:29]C(=O)C)=[N:23][C:24]=2[OH:28])[CH2:8][O:9]CC1C=CC=CC=1)[CH2:2][CH2:3][CH3:4].C1CCCCC=1>[Pd].C(O)C>[NH2:29][C:22]1[N:21]=[C:20]2[C:25]([N:26]=[CH:27][N:19]2[CH2:18][O:17][CH:7]([CH2:8][OH:9])[CH2:6][O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[C:24]([OH:28])[N:23]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 178450471HCID 178450471, compound

Product 1

HCID 178450472HCID 178450472, compoundYield 8.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-[9-[[1-(butoxymethyl)-2-(phenylmethoxy)ethoxy]methyl]-6-hydroxy-9H-purin-2-yl]acetamide (1.15 g, 25.9 mmol), 20% palladium on carbon (0.2 g), cyclohexene (20 ml), and ethanol (10 ml) is heated at reflux under N2. After 8 and 2O hours, additional amounts of catalyst (0.1 g) are added. After 36 hours, the solution is cooled, filtered through celite, and the filter cake is washed with DMF/ethanol. The filtrates are combined, refiltered and concentrated. The residue is mixed with aq. methyl amine (20 ml) and the mixture is heated at reflux for two hours, filtered and concentrated. The residue is recrystallized from water to give the desired product (0.7 g), mp 208°-211° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux under N2
  3. temperaturethe solution is cooled
  4. filtrationfiltered through celite
  5. washthe filter cake is washed with DMF/ethanol
  6. concentrationconcentrated
  7. additionThe residue is mixed with aq. methyl amine (20 ml)
  8. temperaturethe mixture is heated
  9. temperatureat reflux for two hours
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue is recrystallized from water

Sources & evidence

ORD record
ord-8970d29534bc4e4e949f9712940cfbd3
Source dataset
uspto-grants-1992_03
Patent number
US05098906

Reaction notes

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