Sodium Hydroxide → Xanthine

HRID 1742201Notes

Reaction equation

HRID 1742201 reaction equation
C([N:4]1[C:11]([NH2:12])=[C:10]([NH:13][C:14](=O)C)[C:8](=[O:9])[NH:7][C:5]1=[O:6])CC.BrCCCCCO.[OH-].[Na+]>CN(C)C=O>[NH:7]1[C:8](=[O:9])[C:10]2[NH:13][CH:14]=[N:12][C:11]=2[NH:4][C:5]1=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1187091-Pentanol, 5-bromo-HCID 15614028HCID 15614028, compound

Product 1

HCID 1188Xanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.6 g (0.1 mole) of 1-propyl-5-acetylamino-6-aminouracil (II) (R3 =methyl, R8 =methyl) are suspended under nitrogen in 200 ml of anhydrous dimethyl formamide (DMF) . 21.7 g (0.13 mole) of 5-bromo-l-pentanol are then added, after which 6 g (0.15 mole) of powder-form solid NaOH are added with stirring in portions of 1 g at a time at intervals of 1 hour. After the third addition, the suspension is completely dissolved. The solution is left standing overnight to complete the reaction. The solvent is evaporated in a rotary evaporator at 40° C./0.1 mm Hg. The oily residue, which is the uracil (III) (R1 =5-hydroxypentyl, R3 =propyl , R8 =methyl), which is not purified, is dissolved in 100 ml of 10% NaOH and the solution heated under reflux for 2 hours. The solution is then cooled in a ice bath and neutralized to pH 5 with acetic acid. The product precipitated is filtered, washed with cold water and then dried in a vacuum oven. The dried product is dissolved in 500 ml of ethanol and the solution is decoloured overnight with active carbon. The product is precipitated by addition of 1 liter of water, filtered and the treatment with active carbon repeated. The dried product is recrystallized twice with 120 ml of dioxane. Yield: 23.5 g (80%); colourless crystals; Mp. 184-185° C.

Workup

  1. additionAfter the third addition
  2. dissolutionthe suspension is completely dissolved
  3. waitThe solution is left
  4. waitstanding overnight
  5. customthe reaction
  6. customThe solvent is evaporated in a rotary evaporator at 40° C./0.1 mm Hg
  7. customR3 =propyl , R8 =methyl), which is not purified
  8. dissolutionis dissolved in 100 ml of 10% NaOH
  9. temperaturethe solution heated
  10. temperatureunder reflux for 2 hours
  11. temperatureThe solution is then cooled in a ice bath
  12. customThe product precipitated
  13. filtrationis filtered
  14. washwashed with cold water
  15. customdried in a vacuum oven
  16. dissolutionThe dried product is dissolved in 500 ml of ethanol
  17. waitthe solution is decoloured overnight with active carbon
  18. customThe product is precipitated by addition of 1 liter of water
  19. filtrationfiltered
  20. customThe dried product is recrystallized twice with 120 ml of dioxane

Sources & evidence

ORD record
ord-77f034659fe7472aa0aa8e6ae28005c8
Source dataset
uspto-grants-1994_08
Patent number
US05338741

Reaction notes

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