Acetic Anhydride → 3,8-Dimethyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1421230Notes

Reaction equation

HRID 1421230 reaction equation
[CH3:1][N:2]1[C:9]([NH2:10])=[C:8]([NH2:11])[C:6](=[O:7])[NH:5][C:3]1=[O:4].[C:12](OC(=O)C)(=O)[CH3:13]>>[CH3:1][N:2]1[C:9]2[N:10]=[C:12]([CH3:13])[NH:11][C:8]=2[C:6](=[O:7])[NH:5][C:3]1=[O:4]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 1571843-Methyl-4,5-diaminouracil

Product 1

HCID 179959183,8-Dimethyl-3,7-dihydro-1H-purine-2,6-dione

Procedure

A solution of 1-methyl-5,6-diaminouracil (2.5 g) in acetic anhydride (25 ml) was heated at reflux for 2 hours and then concentrated. The residue was dissolved in 10% sodium hydroxide solution (50 ml) and heated at reflux for 2 hours. After cooling to room temperature the solution was acidified to pH 4 with concentrated hydrochloric acid. The product was filtered, washed with water (15 ml), with acetone (15 ml) and then dried under vacuum. Yield 1.8 g.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 10% sodium hydroxide solution (50 ml)
  4. temperatureheated
  5. temperatureat reflux for 2 hours
  6. filtrationThe product was filtered
  7. washwashed with water (15 ml), with acetone (15 ml)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-844250ff3c3a466d861e7c252b8be194
Source dataset
uspto-grants-2000_06
Patent number
US06075029

Reaction notes

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