Formic Acid → 1H-Purine-2,6-dione, 3,7-dihydro-3-(2-methylpropyl)-

HRID 1381858Notes

Reaction equation

HRID 1381858 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[NH:4][C:5](=[O:13])[N:6]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:7]=1[NH2:8].[CH:15](O)=O>>[CH3:12][CH:10]([CH3:11])[CH2:9][N:6]1[C:7]2[N:8]=[CH:15][NH:1][C:2]=2[C:3](=[O:14])[NH:4][C:5]1=[O:13]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 105841095,6-Diamino-1-(2-methylpropyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 30485051H-Purine-2,6-dione, 3,7-dihydro-3-(2-methylpropyl)-

Procedure

A solution of 24.2 g of 5,6-diamino-1-(2-methylpropyl)-2,4-(1H,3H)-pyrimidinedione (XVI) in 60 ml of formic acid was refluxed for 2 hours. The hot solution was filtered and 30 ml of chloroform was added and ether was then added slowly. The received crystals were filtered off. Yield 17.8 g (XVII). The amide (XVII) was refluxed in 50 ml of 2N NaOH for 2 hours and then neutralized with 5N HCl. The crystals were filtered off and recrystallized from ethanol. Yield 11.6 g (46%), NMR. ##STR10##

Workup

  1. filtrationThe hot solution was filtered
  2. addition30 ml of chloroform was added
  3. additionether was then added slowly
  4. filtrationThe received crystals were filtered off
  5. temperatureThe amide (XVII) was refluxed in 50 ml of 2N NaOH for 2 hours
  6. filtrationThe crystals were filtered off
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a3263eb1af304faa8b53f6a5cfa04a29
Source dataset
uspto-grants-1989_02
Patent number
US04804664

Reaction notes

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