HCID 68337899, compound → 1-(2-fluoro-6-(trifluoroMethyl)benzyl)-6-Methyl-5-(piperazin-1-yl)pyriMidine-2,4(1H,3H)-dione

HRID 574247Notes

Reaction equation

HRID 574247 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15](=[O:34])[NH:16][C:17](=[O:33])[N:18]([CH2:21][C:22]3[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:23]=3[F:32])[C:19]=2[CH3:20])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.ClCCl.[Pd]>[F:32][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:31])([F:30])[F:29])[C:22]=1[CH2:21][N:18]1[C:19]([CH3:20])=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:15](=[O:34])[NH:16][C:17]1=[O:33]

Participants

5

Reactant 2

HCID 68337899HCID 68337899, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 671433441-(2-fluoro-6-(trifluoroMethyl)benzyl)-6-Methyl-5-(piperazin-1-yl)pyriMidine-2,4(1H,3H)-dioneYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 5-(4-benzyl-piperazin-1-yl)-1-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-1H-pyrimidine-2,4-dione (1.48 g, 3.11 mmol) in 10 mL of methanol/dichloromethane (1/1) was added 10% palladium/carbon (280 mg), after which the solution was stirred at room temperature for 5 hrs in a hydrogen atmosphere. Following the removal of palladium/carbon therefrom by filtration through cellite, the solution was concentrated. The residue was purified using amine silica gel chromatography (eluent: dichloromethane/methanol, 30/1→10/1) and dried in a vacuum to afford 934 mg of the compound as a white solid. (yield 79%). 1H NMR (300 MHz, CDCl3) δ 2.32 (3H, s), 2.52 (2H, m), 2.83 (2H, m), 2.96 (2H, m), 3.43 (2H, m), 5.37 (2H, s), 7.22 (1H, d), 7.40 (1H, dd), 7.54 (1H, d)

Workup

  1. customthe removal of palladium/carbon
  2. filtrationby filtration through cellite
  3. concentrationthe solution was concentrated
  4. customThe residue was purified
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-932af3e45f13456e9994175cf37df605
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

Loading…