Sodium Hydroxide → 1H-Purine-2,6-dione, 3,7-dihydro-1,3-diethyl-8-(2-(3-methoxyphenyl)ethenyl)-, (E)-

HRID 1378999Notes

Reaction equation

HRID 1378999 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8](O)=O.Cl.C(N(CC)CCCN=C=NCC)C.[NH2:28][C:29]1[C:30](=[O:41])[N:31]([CH2:39][CH3:40])[C:32](=[O:38])[N:33]([CH2:36][CH3:37])[C:34]=1[NH2:35].[OH-].[Na+]>C(Cl)(Cl)Cl.O.O1CCOCC1>[CH2:39]([N:31]1[C:30](=[O:41])[C:29]2[NH:28][C:8](/[CH:7]=[CH:6]/[C:5]3[CH:11]=[CH:12][CH:13]=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:35][C:34]=2[N:33]([CH2:36][CH3:37])[C:32]1=[O:38])[CH3:40]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 871552-Propenoic acid, 3-(3-methoxyphenyl)-HCID 45721335,6-Diamino-1,3-diethyluracilHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Product 1

HCID 64488781H-Purine-2,6-dione, 3,7-dihydro-1,3-diethyl-8-(2-(3-methoxyphenyl)ethenyl)-, (E)-Yield 49%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Methoxycinnamic acid (2.48 g, 13.9 mmol) and 3-(3-diethylaminopropyl)-1-ethylcarbodiimide hydrochloride (3.62 g, 18.9 mmol) were added to a mixture of dioxane (80 ml) and water (40 ml) containing 5,6-diamino-1,3-diethyluracil [J. Am. Chem. Soc., 75, 114 (1953)] (2.5 g, 12.6 mmol). The resulting solution was stirred at room temperature for 2 hours at pH 5.5. After a 4N aqueous solution of sodium hydroxide was added thereto to adjust the pH to >14, 40 ml of water was added and the mixture was heated under reflux for 20 minutes. After cooling, the mixture was neutralized and 50 ml of chloroform was added thereto. The organic layer was separated and the aqueous layer was extracted twice with 50 ml of chloroform. The combined extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was recrystallized from dimethylformamide/water to give 2.10 g (yield 49%) of Compound r as a white powder.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 20 minutes
  4. temperatureAfter cooling
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted twice with 50 ml of chloroform
  7. extractionThe combined extract
  8. washwas washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. customfollowed by evaporation under reduced pressure
  11. customThe residue was recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-fe77290b9a804b8593b59a47dc708f40
Source dataset
uspto-grants-1997_09
Patent number
US05670498

Reaction notes

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