(S)-2-amino-6-(2-fluoro-5-nitro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one → (S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one

HRID 2409125Notes

Reaction equation

HRID 2409125 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([CH3:11])([CH3:10])[C@:4]([C:13]2[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:14]=2[F:22])([CH3:12])[N:3]=1>C(O)C.C(N(CC)CC)C.[Pd]>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([CH3:10])([CH3:11])[C@:4]([C:13]2[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:14]=2[F:22])([CH3:12])[N:3]=1

Participants

5

Reactant 1

HCID 57497156(S)-2-amino-6-(2-fluoro-5-nitro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one

Product 1

HCID 57497157(S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-oneYield 98.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of (S)-2-amino-6-(2-fluoro-5-nitro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (0.55 g) in ethanol (25 ml) and triethylamine (0.25 ml) was added Pd/C (10%, 80 mg) and the mixture was hydrogenated at atmospheric pressure for 3 h. The mixture was filtered, the filtrate evaporated and the residue purified by chromatography on silica using ethyl acetate/MeOH (1:1) to give (S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (0.49 g) as a pale yellow amorphous solid. MS (ESI): m/z=297.2 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customthe residue purified by chromatography on silica

Sources & evidence

ORD record
ord-244f34c1e79747259d74193292287349
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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