Acetic Acid → 3-cyclopropyl-3,7-dihydro-8-methyl-1H-purine-2,6-dione

HRID 464611Notes

Reaction equation

HRID 464611 reaction equation
[CH:1]1([N:4]2[C:9]([NH2:10])=[C:8]([NH2:11])[C:7](=[O:12])[NH:6][C:5]2=[O:13])[CH2:3][CH2:2]1.[C:14](O)(=O)[CH3:15]>>[CH:1]1([N:4]2[C:9]3[N:10]=[C:14]([CH3:15])[NH:11][C:8]=3[C:7](=[O:12])[NH:6][C:5]2=[O:13])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 536900761-cyclopropyl-5,6-diamino-2,4-(1H,3H)-pyrimidinedione

Product 1

HCID 202170533-cyclopropyl-3,7-dihydro-8-methyl-1H-purine-2,6-dione

Procedure

A solution of 6.4 g of 1-cyclopropyl-5,6-diamino-2,4-(1H,3H)-pyrimidinedione (IV) in 20 ml of acetic acid was refluxed for 2 hours. The solution was evaporated. The received oil was refluxed in 40 ml of 2N NaOH and 10 ml of 5N NaOH for 1 hour and then neutralized with 5N HCl. The crystals were filtered off. Yield 1.85 g (26%) (XXXVI) NMR (see Table I).

Workup

  1. customThe solution was evaporated
  2. temperatureThe received oil was refluxed in 40 ml of 2N NaOH
  3. filtrationThe crystals were filtered off

Sources & evidence

ORD record
ord-317c08e389cc4ec9a66a67d693a93c2a
Source dataset
uspto-grants-1985_10
Patent number
US04548818

Reaction notes

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