Potassium Carbonate → 1-amino-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)-phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 380309Notes

Reaction equation

HRID 380309 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])=[CH:6][C:5]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[NH:20][C:19]2=[O:29])=[C:4]([F:30])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N+:37](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C)C=O>[NH2:37][N:20]1[C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][C:23](=[O:24])[N:18]([C:5]2[CH:6]=[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:15]([O-:17])=[O:16])[C:2]([Cl:1])=[CH:3][C:4]=2[F:30])[C:19]1=[O:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 184029813-[4-Chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 113401491-amino-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)-phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneYield 43.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4,-dione (1.0 g), potassium carbonate (0.37 g), and 2,4-dinitrophenoxyamine (0.54 g) in anhydrous N,N-dimethylformamide (20 ml) was stirred at room temperature for 20 hours. The solution was processed and the resulting oil was chromatographed on silica gel eluting with methylene chloride:hexane:ethyl acetate, 2:3:0.5. The product was crystallized from methylene chloride:hexane:ethyl acetate to give a white solid (0.45 g).

Workup

  1. customthe resulting oil was chromatographed on silica gel eluting with methylene chloride
  2. customThe product was crystallized from methylene chloride

Sources & evidence

ORD record
ord-e6cd0dff74ee4f8e8b88bd10188bab71
Source dataset
uspto-grants-2001_10
Patent number
US06303543B1

Reaction notes

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