Triethylamine → HCID 18981945, compound

HRID 1440781Notes

Reaction equation

HRID 1440781 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)=[CH:12][N:11]=[C:10]([CH3:17])[N:9]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.C([N:37]([CH2:40]C)CC)C.[CH2:42]([C:44]1[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][CH3:52])[C:45]=1[NH2:46])[CH3:43]>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:37][C:40]([NH:46][C:45]2[C:47]([CH2:51][CH3:52])=[CH:48][CH:49]=[CH:50][C:44]=2[CH2:42][CH3:43])=[O:25])=[CH:12][N:11]=[C:10]([CH3:17])[N:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 113692,6-DiethylanilineHCID 199401P,P-Diphenylphosphinic azideHCID 18981951HCID 18981951, compound

Product 1

HCID 18981945HCID 18981945, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 373 mg of 4-(2-chlorophenyl)-2-methyl-5-pyrimidinecarboxylic acid and 0.39 cc of diphenylphosphoryl azide in 5 cc of benzene was added dropwise 0.22 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 30 minutes and then heated under reflux for 30 minutes. After cooling, 0.3 cc of 2,6-diethylaniline was added, followed by refluxing for 3 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=3/2) to obtain 510 mg of compound 45.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. temperatureby refluxing for 3 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=3/2)

Sources & evidence

ORD record
ord-c2650dc571ca4cdf980b12dc92dea6f7
Source dataset
uspto-grants-1996_03
Patent number
US05500424

Reaction notes

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