Formamidine acetate → 9-Deazahypoxanthine

HRID 751249Notes

Reaction equation

HRID 751249 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-d8d6f5d1d9114105a211a6aa2bfa13b0
Source dataset
uspto-grants-2008_07
Patent number
US07405297B2

Reaction notes

Loading…