(4R)-4-(4-Cyano-2-nitrophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile → HCID 66734667, compound

HRID 2361910Notes

Reaction equation

HRID 2361910 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[N:12]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:11](=[O:28])[NH:10]2)=[C:5]([N+:29]([O-])=O)[CH:4]=1)#[N:2]>C(O)C.[Pd]>[NH2:29][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=1[C@@H:9]1[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[N:12]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:11](=[O:28])[NH:10]1

Participants

4

Reactant 1

HCID 66601717(4R)-4-(4-Cyano-2-nitrophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile

Product 1

HCID 66734667HCID 66734667, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under argon, (4R)-4-(4-cyano-2-nitrophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (39.5 g, 92.4 mmol) was dissolved in ethanol (1975 ml). 10% Palladium on activated carbon (19.8 g) was then added, and the mixture was hydrogenated at RT and atmospheric pressure for 2 h (strictly monitored by TLC). The reaction mixture was then filtered through kieselguhr. The filtrate was concentrated and the crude product obtained was subjected to flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 2:1). The title compound was obtained as a solid (25.5 g, 68% of theory).

Workup

  1. customwas hydrogenated at RT
  2. filtrationThe reaction mixture was then filtered through kieselguhr
  3. concentrationThe filtrate was concentrated
  4. customthe crude product obtained

Sources & evidence

ORD record
ord-501611aa6af54e6cb504aa6bb63d2f6a
Source dataset
uspto-grants-2014_04
Patent number
US08691817B2

Reaction notes

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