Ammonia → 6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-3H-pyrimidin-4-one

HRID 1891007Notes

Reaction equation

HRID 1891007 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[NH:17][C:16](=S)[NH:15][C:14](=[O:19])[CH:13]=1.N.[CH3:21][CH2:22]O>[Ni]>[O:2]1[CH2:1][CH2:22][CH2:21][CH:3]1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:17]=[CH:16][NH:15][C:14](=[O:19])[CH:13]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 58550539HCID 58550539, compound

Product 1

HCID 1361275726-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

6-[2-(2-methoxy-ethoxy)-phenyl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (0.6 g, 1.97 mmol) is dissolved in EtOH (12 mL) and aqueous solution of ammonia (25%, 4 mL). After addition of Raney-Nickel (0.5 g) the reaction mixture is stirred under reflux for 1 h, filtered from the solid material, which is washed with a mixture of ammonia and EtOH. The combined solutions were evaporated, dissolved in water (10 mL), neutralized with 10% HCl and extracted with ethyl acetate (3×15 mL). Organic layers were combined, washed with water (7 mL) then dried over anhydrous sodium sulfate and concentrated. The residue was triturated with diethyl ether yielding 0.47 g (87%) 6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-3H-pyrimidin-4-one as cream powder.

Workup

  1. temperatureunder reflux for 1 h
  2. filtrationfiltered from the solid material, which
  3. washis washed with a mixture of ammonia and EtOH
  4. customThe combined solutions were evaporated
  5. dissolutiondissolved in water (10 mL)
  6. extractionextracted with ethyl acetate (3×15 mL)
  7. washwashed with water (7 mL)
  8. dry with materialthen dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was triturated with diethyl ether yielding 0.47 g (87%) 6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-3H-pyrimidin-4-one as cream powder

Sources & evidence

ORD record
ord-5a567bf13dff4c8cbc9d389f4a98f788
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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