Benzoic Acid → 8-Phenyl-1,3-dipropyl-3,9-dihydro-1H-purine-2,6-dione

HRID 1981584Notes

Reaction equation

HRID 1981584 reaction equation
[CH2:1]([N:4]1[C:11]([NH2:12])=[C:10]([NH2:13])[C:8](=[O:9])[N:7]([CH2:14][CH2:15][CH3:16])[C:5]1=[O:6])[CH2:2][CH3:3].[C:17](O)(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH2:14]([N:7]1[C:8](=[O:9])[C:10]2[NH:13][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][C:11]=2[N:4]([CH2:1][CH2:2][CH3:3])[C:5]1=[O:6])[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 1287848-Phenyl-1,3-dipropyl-3,9-dihydro-1H-purine-2,6-dioneYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,3-dipropyl-5,6-diaminouracil (0.01 mol) was dissolved in 30 ml methanol, followed by 0.01 mol of benzoic acid and then 0.01 mol of DICD. The solution was stirred for 30 min at room temperature, filtered, and washed with a small amount of methanol. The solid was boiled for ten minutes in 2.5N KOH, filtered hot, and the liquid neutralized with concentrated HCl. The solid was collected by filtration, washed with water, redissolved in 100 ml with a minimum amount of KOH, precipitated by neutralization with HCL, filtered, washed with water, and dried. The product was identified by chemical ionization mass spectrometry and elemental analysis. Yield 77%.

Workup

  1. filtrationfiltered
  2. washwashed with a small amount of methanol
  3. waitThe solid was boiled for ten minutes in 2.5N KOH
  4. filtrationfiltered hot
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. dissolutionredissolved in 100 ml with a minimum amount of KOH
  8. customprecipitated by neutralization with HCL
  9. filtrationfiltered
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-0462b2d84e6240458c85d00454c61e8b
Source dataset
uspto-grants-1986_06
Patent number
US04593095

Reaction notes

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