Formamidine acetate → Tert-butyl 4-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate

HRID 1616085Notes

Reaction equation

HRID 1616085 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][S:5][C:6]=1[C:7](OCC)=[O:8].C(O)(=O)C.[CH:29](N)=[NH:30]>C(O)C>[O:8]=[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]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]3)=[CH:4][S:5][C:6]1=2

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 86681876Tert-butyl 4-[4-amino-5-(ethoxycarbonyl)thiophen-3-yl]piperidine-1-carboxylate

Product 1

HCID 136359802Tert-butyl 4-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylateYield 21.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 4-[4-amino-5-(ethoxycarbonyl)thiophen-3-yl]piperidine-1-carboxylate (307 mg, 0.87 mmol) was dissolved in ethanol (8 mL), and then formamidine acetate (542 mg, 5.20 mmol) was added, followed by heating under reflux for 36 hours. The reaction liquid was concentrated under a reduced pressure, and the obtained residue was dissolved in chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The obtained residue was purified by using silica gel chromatography (chloroform:methanol=10:1) to give tert-butyl 4-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate (62.5 mg, 21.5%) as a pale yellow amorphous.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 36 hours
  3. customThe reaction liquid
  4. concentrationwas concentrated under a reduced pressure
  5. dissolutionthe obtained residue was dissolved in chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. customThe obtained residue was purified

Sources & evidence

ORD record
ord-1f7c8ed7417d4b6e9b6af55b9f6da7ec
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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