Sodium Hydroxide → Xanthine

HRID 1742202Notes

Reaction equation

HRID 1742202 reaction equation
C([N:5]1[C:12]([NH2:13])=[C:11]([NH:14][CH:15]=O)[C:9](=[O:10])[NH:8][C:6]1=[O:7])CCC.BrCCCC(OCC)=O.[OH-].[Na+]>CN(C=O)C>[NH:8]1[C:9](=[O:10])[C:11]2[NH:14][CH:15]=[N:13][C:12]=2[NH:5][C:6]1=[O:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrateHCID 15931311HCID 15931311, compound

Product 1

HCID 1188Xanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11.3 g (0 . 05 mole) of 1-butyl-5-formylamino-6-aminouracil (II) (R1 =butyl, R8 =H) are dissolved under nitrogen in 200 ml of DMF. 10.6 ml (0.075 mole) of ethyl 4-bromobutyrate are added, after which 2 g (0.05 mole) of solid powder-form NaOH is added with thorough stirring in portions of 0.5 g at intervals of 1 hour. On completion of the addition, the mixture is left to react overnight. The solvent is then evaporated and the oily residue of (IV) (substituent in the 1-position=(CH2)3COOEt) is dissolved in 100 ml of 10% NaOH. This solution is then heated under reflux for 0.5 hour and then cooled, neutralized to pH 5 with acetic acid and filtered. The precipitate formed is dried. Yield: 9.2 g (60%) of crude xanthine (V) (substituent in the 1-position=(CH2)3COOH, R3 =butyl, R8 =H).

Workup

  1. additionOn completion of the addition
  2. waitthe mixture is left
  3. customto react overnight
  4. customThe solvent is then evaporated
  5. dissolutionthe oily residue of (IV) (substituent in the 1-position=(CH2)3COOEt) is dissolved in 100 ml of 10% NaOH
  6. temperatureThis solution is then heated
  7. temperatureunder reflux for 0.5 hour
  8. temperaturecooled
  9. filtrationfiltered
  10. customThe precipitate formed
  11. customis dried

Sources & evidence

ORD record
ord-52274122096b4492b1622e10f56b0ba3
Source dataset
uspto-grants-1994_08
Patent number
US05338741

Reaction notes

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