Water → HCID 57098099, compound

HRID 1271765Notes

Reaction equation

HRID 1271765 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 vacuo 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 vacuo
  6. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d3b5414778ad484dadada8c35d757a18
Source dataset
uspto-grants-2007_04
Patent number
USRE039590E1

Reaction notes

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