Ethanol → 3,7-dihydro-8-methyl-3-propyl-1H-purine-2,6-dione

HRID 236309Notes

Reaction equation

HRID 236309 reaction equation
[NH2:1][C:2]1[C:3](=[O:13])[NH:4][C:5](=[O:12])[N:6]([CH2:9][CH2:10][CH3:11])[C:7]=1[NH2:8].[CH2:14](O)[CH3:15]>C(O)(=O)C>[CH3:14][C:15]1[NH:1][C:2]2[C:3](=[O:13])[NH:4][C:5](=[O:12])[N:6]([CH2:9][CH2:10][CH3:11])[C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 106313415,6-Diamino-1-propyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 202170503,7-dihydro-8-methyl-3-propyl-1H-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 22.6 g of 5,6-diamino-1-propyl-2,4-(1H,3H)-pyrimidinedione in 50 ml of acetic acid was refluxed for 2 hours. 30 ml of ethanol was added. The received crystals were filtered off. Yield 19.8 g. The amide was refluxed in 80 ml of 2N NaOH for 2 hours and then neutralized with 5N HCl. The crystals were filtered off and recrystallized from 2.1 l ethanol. Yield 9.8 g (38%) (XXXXVI) NMR (see Table I).

Workup

  1. filtrationThe received crystals were filtered off
  2. temperatureThe amide was refluxed in 80 ml of 2N NaOH for 2 hours
  3. filtrationThe crystals were filtered off
  4. customrecrystallized from 2.1 l ethanol

Sources & evidence

ORD record
ord-53f91be1b9e8435dbf46f9dfd95ed382
Source dataset
uspto-grants-1987_02
Patent number
US04644001

Reaction notes

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