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

HRID 464598Notes

Reaction equation

HRID 464598 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). ##STR9##

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-84913365092a4ba799fa85d9de279ccd
Source dataset
uspto-grants-1985_10
Patent number
US04548818

Reaction notes

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