HCID 9805180, compound → HCID 9908433, compound

HRID 1977233Notes

Reaction equation

HRID 1977233 reaction equation
C([N:8]1[CH:13]=[C:12]([CH3:14])[C:11](=[O:15])[N:10]([CH2:16][CH2:17][CH2:18][NH:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[O:33][CH3:34])[CH2:22][CH2:21]2)[C:9]1=[O:35])C1C=CC=CC=1>CO.C([O-])=O.[NH4+].[Pd]>[F:32][C:29]1[CH:30]=[CH:31][C:26]([N:23]2[CH2:22][CH2:21][CH:20]([NH:19][CH2:18][CH2:17][CH2:16][N:10]3[C:11](=[O:15])[C:12]([CH3:14])=[CH:13][NH:8][C:9]3=[O:35])[CH2:25][CH2:24]2)=[C:27]([O:33][CH3:34])[CH:28]=1

Participants

5

Reactant 1

HCID 9805180HCID 9805180, compound

Product 1

HCID 9908433HCID 9908433, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 2723923Ammonium formateSolvent

Procedure

1-Benzyl-3-{3-[1-(4-fluoro-2-methoxyphenyl)piperidin-4-ylamino]propyl}-5-methyl-1H-pyrimidine-2,4-dione (Example 8) (100 mg, 0.2 mmol) was dissolved in a methanol solution of ammonium formate (0.1 M, 20 mL), treated with 10% palladium on carbon (100 mg) and the reaction heated to reflux for 24 h. The reaction mixture was filtered through a pad of celite, the filtrate concentrated and purified by pressurized silica gel chromatography (97.5:2:0.5 dichloromethane:methanol:ammonium hydroxide) to provide 3-{3-[1-(4-fluoro-2-methoxyphenyl)piperidin-4-ylamino]propyl}-5-methyl-1H-pyrimidine-2,4-dione. The hydrochloride salt was prepared according to conventional methods to provide a white solid.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 24 h
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationthe filtrate concentrated
  5. custompurified by pressurized silica gel chromatography (97.5:2:0.5 dichloromethane:methanol:ammonium hydroxide)

Sources & evidence

ORD record
ord-dbc10de42cce4bddbc63845df30fdd26
Source dataset
uspto-grants-2001_05
Patent number
US06232318B1

Reaction notes

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