Water → 3-(2-amino-4-chloro-6-fluoro-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 277423Notes

Reaction equation

HRID 277423 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([N+:22]([O-])=O)[C:3]=1[CH3:25].O>C(O)(=O)C.[Fe]>[NH2:22][C:4]1[C:3]([CH3:25])=[C:2]([Cl:1])[CH:7]=[C:6]([F:8])[C:5]=1[N:9]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]1=[O:21]

Participants

5

Reactant 2

HCID 962WaterHCID 569910913-(4-Chloro-6-fluoro-3-methyl-2-nitrophenyl)-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Product 1

HCID 865859023-(2-amino-4-chloro-6-fluoro-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

3-(4-Chloro-6-fluoro-3-methyl-2-nitrophenyl)-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (2.0 g, 5.2 mmol) was dissolved in acetic acid (20 ml) and iron powder (1.2 g, 21.5 mmol) was added. Solution was stirred at ambient temperature for 14 hr. Water was added and product extracted with ethyl acetate followed by evaporation under reduced pressure. Title compound was separated by column chromatography on silica gel (eluent, hexane-ethyl acetate, 7:3; 1.5 g).

Workup

  1. extractionproduct extracted with ethyl acetate
  2. customfollowed by evaporation under reduced pressure
  3. customTitle compound was separated by column chromatography on silica gel (eluent, hexane-ethyl acetate, 7:3; 1.5 g)

Sources & evidence

ORD record
ord-aa26351302854178a7ac4e1ebb1c4450
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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