Triethylamine → 3-[4-chloro-6-fluoro-3-methoxy-2-(2-naphthoyloxy)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 1265396Notes

Reaction equation

HRID 1265396 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]([OH:22])[C:3]=1[O:23][CH3:24].[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[C:35](Cl)=[O:36].C(N(CC)CC)C>O1CCOCC1>[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:17])[F:18])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([O:22][C:35]([C:26]2[CH:27]=[CH:28][C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:25]=2)=[O:36])[C:3]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 572512883-(4-chloro-6-fluoro-2-hydroxy-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Product 1

HCID 867578643-[4-chloro-6-fluoro-3-methoxy-2-(2-naphthoyloxy)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(4-chloro-6-fluoro-2-hydroxy-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.10 g, 0.27 mmol) was dissolved in dioxane (10 ml) and the solution added with 2-naphthoyl chloride (0.062 g, 0.33 mmol), triethylamine (0.033 g, 0.33 mmol). After stirred for 2 hr, solvent was evaporated and the residue purified by column chromatography (silica gel, hexane/ether=4/1). Yield: 0.12 g, 0.23 mmol.

Workup

  1. customsolvent was evaporated
  2. customthe residue purified by column chromatography (silica gel, hexane/ether=4/1)

Sources & evidence

ORD record
ord-7f2cefef50034944a183e1b3a05448d0
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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