HCID 18402912, compound → HCID 18402937, compound

HRID 1017184Notes

Reaction equation

HRID 1017184 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[C:18]([F:21])([F:20])[F:19])=[CH:6][C:5]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[NH:24][C:23]2=[O:33])=[C:4]([F:34])[CH:3]=1>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[C:18]([F:21])([F:19])[F:20])=[CH:6][C:5]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:31])([F:30])[F:32])[NH:24][C:23]2=[O:33])=[C:4]([F:34])[CH:3]=1

Participants

4

Reactant 1

HCID 18402912HCID 18402912, compound

Product 1

HCID 18402937HCID 18402937, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 10% Pd/C and 3-[4-chloro-2-fluoro-5-(4-nitro-2-trifluoromethylphenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (4.0 g) in ethyl acetate (100 ml) was stirred overnight under an atmosphere of hydrogen. The mixture was filtered through Celite and the filtrate concentrated. The resulting oil was chromatographed on silica gel eluting with ethyl acetate:hexane, 1:0.8.3-[4-Chloro-2-fluoro-5-(4-amino-2-trifluoromethylphenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (Intermediate 11-24) was isolated as an amorphous solid (33 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated
  3. customThe resulting oil was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-1b2c4054b29c443dbf7a695984e1b375
Source dataset
uspto-grants-2002_11
Patent number
US06479435B1

Reaction notes

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