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

HRID 1265388Notes

Reaction equation

HRID 1265388 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=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].[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[C:32](Cl)=[O:33].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([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:2]([NH:1][C:32]([C:23]2[CH:24]=[CH:25][C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:22]=2)=[O:33])[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 865859053-(2-amino-4-chlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Product 1

HCID 571796353-[4-chloro-2-(2-naphthoylamino)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedioneYield 70.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(2-amino-4-chlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.4 g), 2-naphthoyl chloride (0.29 g) and triethyl amine (0.19 g) in anhydrous tetrahydro furan (30 ml) was heated at reflux temperature overnight under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate (200 ml), washed with brine (×2) and dried over anhydrous sodium sulfate. The solvent was removed unded reduced pressure and the residue was purified by column chromatography on silica gel using ethyl acetate and hexane (1:3) as the eluent give a pale yellow solid. The solid was recrystallized from ethyl acetate-hexane to give the title compound as a white crystal (0.42 g).

Workup

  1. temperatureat reflux temperature overnight under nitrogen atmosphere
  2. washwashed with brine (×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed unded reduced pressure
  5. customthe residue was purified by column chromatography on silica gel
  6. customgive a pale yellow solid
  7. customThe solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-969d2b771296488fa7269a68ee059dcd
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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