Triethylamine → HCID 15818749, compound

HRID 1440779Notes

Reaction equation

HRID 1440779 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13](C(O)=O)=[C:12]([CH3:17])[N:11]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C([N:43]([CH2:46]C)CC)C.[CH:48]([C:51]1[CH:57]=[CH:56][CH:55]=[C:54]([CH3:58])[C:52]=1[NH2:53])([CH3:50])[CH3:49]>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([NH:43][C:46]([NH:53][C:52]2[C:54]([CH3:58])=[CH:55][CH:56]=[CH:57][C:51]=2[CH:48]([CH3:50])[CH3:49])=[O:31])=[C:12]([CH3:17])[N:11]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 789206-Isopropyl-o-toluidineHCID 199401P,P-Diphenylphosphinic azideHCID 15818756HCID 15818756, compound

Product 1

HCID 15818749HCID 15818749, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 325 mg of 4-(2-chlorophenyl)-6-methyl-2-phenyl-5-pyrimidinecarboxylic acid and 0.26 cc of diphenylphosphoryl azide in 5 cc of benzene was added dropwise 0.14 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 20 minutes and then heated under reflux for 20 minutes. After cooling, 0.18 cc of 2-isopropyl-6-methylaniline was added, followed by refluxing for 2 hours. After cooling, water was added to the reaction mixture and extracted with chloroform. The extract was dried over magnesium sulfate, and distilled to remove the solvent. The crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate-hexane) to obtain 350 mg of compound 1.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 minutes
  3. temperatureAfter cooling
  4. temperatureby refluxing for 2 hours
  5. temperatureAfter cooling
  6. extractionextracted with chloroform
  7. dry with materialThe extract was dried over magnesium sulfate
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe crude product thus obtained
  11. customwas purified by a silica gel column chromatography (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ff56600c22fc430388afbcb9e9b9fb4f
Source dataset
uspto-grants-1996_03
Patent number
US05500424

Reaction notes

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