Hydrochloric Acid → 1H-Purine-2,6-dione, 3,7-dihydro-8-(2-(2-chloro-3,4-dimethoxyphenyl)ethenyl)-1,3-dimethyl-, (E)-

HRID 1077495Notes

Reaction equation

HRID 1077495 reaction equation
[Cl:1][C:2]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6](O)=O.S(Cl)(Cl)=O.[NH2:21][C:22]1[C:23](=[O:32])[N:24]([CH3:31])[C:25](=[O:30])[N:26]([CH3:29])[C:27]=1[NH2:28].Cl>N1C=CC=CC=1.[OH-].[Na+].O1CCOCC1.O.C(Cl)Cl>[Cl:1][C:2]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[CH:9][C:3]=1/[CH:4]=[CH:5]/[C:6]1[NH:21][C:22]2[C:23](=[O:32])[N:24]([CH3:31])[C:25](=[O:30])[N:26]([CH3:29])[C:27]=2[N:28]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 795015,6-Diamino-1,3-dimethyluracilHCID 27749672-Chloro-3,4-dimethoxycinnamic acid

Product 1

HCID 64488901H-Purine-2,6-dione, 3,7-dihydro-8-(2-(2-chloro-3,4-dimethoxyphenyl)ethenyl)-1,3-dimethyl-, (E)-Yield 30%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloro-3,4-dimethoxycinnamic acid (3.93 g, 16.2 mmol) was dissolved in 57 ml of pyridine. To the solution was added 1.26 ml (17.6 mmol) of thionyl chloride under ice cooling, and the mixture was stirred at 60° C. for 1.5 hours. Methylene chloride (58 ml) containing 2.50 g (14.7 mmol) of 5,6-diamino-1,3-dimethyluracil was added dropwise to the solution under ice cooling, and the reaction solution was stirred at room temperature for further 40 minutes. The deposited crystals were collected by filtration and the obtained crude crystals were dissolved in a mixture of 68 ml of an aqueous 2N sodium hydroxide solution, 68 ml of dioxane, and 34 ml of water, followed by heating under reflux for 30 minutes. After cooling, the solution was neutralized with a concentrated aqueous solution of hydrochloric acid, and the deposited crystals were collected by filtration. The collected crystals were washed with water, dried, and recrystallized from dimethylformamide/water to give 1.55 g (yield 30%) of Compound 107 as pale yellow needles.

Workup

  1. additionwas added dropwise to the solution under ice cooling
  2. stirringthe reaction solution was stirred at room temperature for further 40 minutes
  3. filtrationThe deposited crystals were collected by filtration
  4. customthe obtained crude crystals
  5. temperatureby heating
  6. temperatureunder reflux for 30 minutes
  7. temperatureAfter cooling
  8. filtrationthe deposited crystals were collected by filtration
  9. washThe collected crystals were washed with water
  10. customdried
  11. customrecrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-c85c8b8a2ea24794a64f06132807e690
Source dataset
uspto-grants-1996_08
Patent number
US05543415

Reaction notes

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