Formamidine acetate → 9-Deazahypoxanthine

HRID 2120997Notes

Reaction equation

HRID 2120997 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].N[C:9]1[CH:13]=[CH:12][NH:11][C:10]=1[C:14](OCC)=[O:15]>C(O)C>[N:6]1[C:9]2[CH:13]=[CH:12][NH:11][C:10]=2[C:14](=[O:15])[NH:7][CH:5]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylate

Product 1

HCID 1354888819-DeazahypoxanthineYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Formamidine acetate (20 g, 0.19 mol.) was added to a solution of crude 2-ethoxycarbonyl-3-aminopyrrole (14) (15.3 g, 0.1 mol.) in ethanol (150 ml) and the solution was heated under reflux for 16 h and then cooled. The solid formed was filtered, washed with ethanol and dried to give 3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (1) (11.5 g, 85.2 mmol.). Recrystallized from water it had mp>300° C. 1H NMR (d6-DMSO) was as reported3. 13C NMR δ 154.0, 145.0, 141.8, 127.7, 118.2, 103.3.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 16 h
  3. temperaturecooled
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with ethanol
  7. customdried

Sources & evidence

ORD record
ord-d3d9119bd17346fea48d84e3a77b25f5
Source dataset
uspto-grants-2004_02
Patent number
US06693193B1

Reaction notes

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