Formamidine acetate → 9-Deazahypoxanthine

HRID 242840Notes

Reaction equation

HRID 242840 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9]CC)=O.C(O)(=O)C.[CH:16](N)=[NH:17]>C(O)C>[N:1]1[C:2]2[CH:6]=[CH:5][NH:4][C:3]=2[C:7](=[O:9])[NH:17][CH:16]=1

Participants

4

Reactant 2

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

Product 1

HCID 1354888819-DeazahypoxanthineYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 250-mL round-bottom flask was placed a solution of ethyl 3-amino-1H-pyrrole-2-carboxylate (10 g, 58.38 mmol, 1.00 equiv, 90%) in ethanol (150 mL) and formamidine acetate (10 g, 94.13 mmol, 1.61 equiv, 98%). The resulting solution was stirred at reflux for 16 h. The precipitates were collected by filtration, washed with ethanol and dried under reduced pressure to afford 5 g (61%) of 3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one as a gray solid

Workup

  1. customInto a 250-mL round-bottom flask was placed
  2. temperatureat reflux for 16 h
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with ethanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-032b18a7d9a542aabfa880d40eec7a67
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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