Triethylamine → 3-[4-chloro-6-fluoro3-methyl-2-(2-naphthoyl)aminophenyl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 1265380Notes

Reaction equation

HRID 1265380 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]1=[O:23].C(N(CC)CC)C.[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[C:41](Cl)=[O:42]>O1CCOCC1>[Cl:9][C:6]1[CH:5]=[C:4]([F:10])[C:3]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[C:2]([NH:1][C:41]([C:32]2[CH:33]=[CH:34][C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:31]=2)=[O:42])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 865859023-(2-amino-4-chloro-6-fluoro-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Product 1

HCID 865859033-[4-chloro-6-fluoro3-methyl-2-(2-naphthoyl)aminophenyl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(2-Amino-4-chloro-6-fluoro-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.5 g, 1.4 mmol) was dissolved in 1,4-dioxane (20 ml) and triethyl amine (0.29 g, 2.9 mmol) and 2-naphthoyl chloride (0.41 g, 2.2 mmol) were added. Solution was heated under reflux for 4 hr and solvent removed under reduced pressure. Product was subjected to column chromatography on silica gel and the title compound was eluted with hexane-ethyl acetate (8:2; 0.3 g).

Workup

  1. temperatureSolution was heated
  2. temperatureunder reflux for 4 hr
  3. customsolvent removed under reduced pressure
  4. washthe title compound was eluted with hexane-ethyl acetate (8:2; 0.3 g)

Sources & evidence

ORD record
ord-a0777754cbee4555beed757a6b4ca036
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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