Formic Acid → 1H-Purine-2,6-dione, 3,7-dihydro-3-cyclopropyl-

HRID 236293Notes

Reaction equation

HRID 236293 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.[CH:14](O)=O>>[CH:1]1([N:4]2[C:9]3[N:10]=[CH:14][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 284Formic AcidHCID 536900761-cyclopropyl-5,6-diamino-2,4-(1H,3H)-pyrimidinedione

Product 1

HCID 30589961H-Purine-2,6-dione, 3,7-dihydro-3-cyclopropyl-

Procedure

A solution of 12 g of 1-cyclopropyl-5,6-diamino-2,4-(1H,3H)-pyrimidinedione (IV) in 50 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 11.2 g (V). The amide (V) was refluxed in 40 ml of 2N NaOH for 1 hour and then neutralized with 5N HCl. The crystals were filtered off. Yield 7 g (60%) (VI) NMR (see Table I).

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 (V) was refluxed in 40 ml of 2N NaOH for 1 hour
  6. filtrationThe crystals were filtered off

Sources & evidence

ORD record
ord-4af039f1ef5641d799e9a93d12bc2042
Source dataset
uspto-grants-1987_02
Patent number
US04644001

Reaction notes

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