Formamidine acetate → tert-butyl 4-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate

HRID 1616087Notes

Reaction equation

HRID 1616087 reaction equation
[NH2:1][C:2]1[C:3]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:4][NH:5][C:6]=1[C:7]([O:9]CC)=O.C(O)(=O)C.[CH:29](N)=[NH:30]>C(O)C>[O:9]=[C:7]1[NH:30][CH:29]=[N:1][C:2]2[C:3]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[CH:4][NH:5][C:6]1=2

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 86681878tert-butyl 4-[4-amino-5-(ethoxycarbonyl)-1H-pyrrol-3-yl]piperidine-1-carboxylate

Product 1

HCID 136359803tert-butyl 4-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylateYield 102.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 4-[4-amino-5-(ethoxycarbonyl)-1H-pyrrol-3-yl]piperidine-1-carboxylate (466 mg, 1.38 mmol) was dissolved in ethanol (8 mL), and then formamidine acetate (863 mg, 8.29 mmol) was added, followed by heating under reflux for 14 hours. The reaction liquid was cooled, and the precipitated solid was filtered and washed with ethanol to give tert-butyl 4-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate (452 mg, >1000) as a pale yellow solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 14 hours
  3. customThe reaction liquid
  4. temperaturewas cooled
  5. filtrationthe precipitated solid was filtered
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-faf481bf407044ebba0534fb8efb0f40
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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