Formamidine acetate → 9-Deazahypoxanthine

HRID 588410Notes

Reaction equation

HRID 588410 reaction equation
Cl.[NH2:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1[C:8]([O:10]CC)=O.C(O)(=O)C.[CH:17](N)=[NH:18]>CCO>[N:2]1[C:3]2[CH:7]=[CH:6][NH:5][C:4]=2[C:8](=[O:10])[NH:18][CH:17]=1

Participants

4

Reactant 2

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

Product 1

HCID 1354888819-DeazahypoxanthineYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
83 °C

Procedure

Ethyl 3-amino-1H-pyrrole-2-carboxylate hydrochloride (3.00 g, 15.7 mmol) was dissolved in EtOH (40 mL). Formamidine acetic acid salt (2.44 g, 23.5 mmol) was added and the reaction mixture was heated under reflux at 83° C. for 18 h. The reaction mixture was cooled to r.t. and the precipitate was collected by filtration, washed with EtOH and dried in vacuo to give the title compound as a beige solid (1.70 g, 80%). LCMS (ES+): 135.9 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureThe reaction mixture was cooled to r.t.
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with EtOH
  5. customdried in vacuo

Sources & evidence

ORD record
ord-aba5277fc3314685aa6d05bc7e96db11
Source dataset
uspto-grants-2016_01
Patent number
US09227967B2

Reaction notes

Loading…