Water → HCID 57098099, compound

HRID 277432Notes

Reaction equation

HRID 277432 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([F:9])[C:3]=1[N:10]1[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]1=[O:22].C(N(CC)CC)C.[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]=1[C:40](Cl)=[O:41].O>O1CCCC1>[Cl:8][C:6]1[CH:5]=[C:4]([F:9])[C:3]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]2=[O:22])=[C:2]([NH:1][C:40]([C:31]2[CH:32]=[CH:33][C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:30]=2)=[O:41])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 86585906HCID 86585906, compound

Product 1

HCID 57098099HCID 57098099, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2-amino-4-chloro-6-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.25 g), triethylamine (0.15 g) and 2-naphthoyl chloride (0.21 g) in anhydrous tetrahydrofuran (30 ml) was heated at refluxtemperature overnight under nitrogen atmosphere. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium acetate. The solvent was removed in vecuo and the residue was purified by column chromatography on silica gel using ethyl acetate-hexane (1:4) as the eluent to give the title compound as an white solid (0.26 g).

Workup

  1. temperaturewas heated at refluxtemperature overnight under nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium acetate
  5. customThe solvent was removed in vecuo
  6. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d71eb39b4ad54036817ff5733197a476
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

Loading…