Formamidine acetate → 9-Deazahypoxanthine

HRID 244446Notes

Reaction equation

HRID 244446 reaction equation
Cl.C(O[C:5]([C:7]1[NH:8][CH:9]=[CH:10][C:11]=1[NH2:12])=[O:6])C.C(O)(=O)C.[CH:17](N)=[NH:18]>CCO>[N:12]1[C:11]2[CH:10]=[CH:9][NH:8][C:7]=2[C:5](=[O:6])[NH:18][CH:17]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 164270913-Amino-2-ethoxycarbonylpyrrole hydrochloride

Product 1

HCID 1354888819-DeazahypoxanthineYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-amino-1H-pyrrole-2-carboxylic acid ethyl ester hydrochloride (3.4 g, 17.7 mmol, 1 equiv.) in 40 mL of EtOH was added formamidine acetic acid salt (2.8 g, 26.6 mmol) and the mixture warmed at 110° C. After 18 hours, the reaction was cool to room temperature and the solids were filtered, rinsed with EtOH, and dried to provide 1.92 g (80%) of 3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one as a beige solid.

Workup

  1. temperaturethe reaction was cool to room temperature
  2. filtrationthe solids were filtered
  3. washrinsed with EtOH
  4. customdried

Sources & evidence

ORD record
ord-588283fa23a7406abc8a95133cb68dac
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

Loading…