2,4,6-Trimethylpyridine → HCID 178435492, compound

HRID 1741243Notes

Reaction equation

HRID 1741243 reaction equation
[CH3:1][CH2:2][C:3]1[C:21]2=[N:22][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[CH:34]([CH3:35])[CH:33]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:15]([C:16]5[CH:27](C(OC)=O)[C:25](=[O:26])[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:32])=[CH:20]2)=[N:14]4)=[C:9]([CH3:42])[C:8]=3[CH:43]=[CH2:44])[C:4]=1[CH3:45].N1C(C)=CC(C)=CC=1C>CCCCCC.CC(C)=O>[CH3:1][CH2:2][C:3]1[C:21]2=[N:22][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[C@@H:34]([CH3:35])[C@H:33]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:15]([C:16]5[CH2:27][C:25](=[O:26])[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:32])=[CH:20]2)=[N:14]4)=[C:9]([CH3:42])[C:8]=3[CH:43]=[CH2:44])[C:4]=1[CH3:45]

Participants

4

Reactant 2

HCID 79532,4,6-TrimethylpyridineHCID 178435494HCID 178435494, compound

Product 1

HCID 178435492HCID 178435492, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21880519Acetone hexaneSolvent

Procedure

Methyl pheophorbide-a (100 mg, 0.17 mmol) was added to 2,4,6-collidine (25 mL, distilled) and the mixture was refluxed under argon with stirring. The reaction was monitored by HPLC (hexane-acetone, 90:10-mobile phase, LiChrospherCN-column, detection at 425 and 410 nm). After 20 min, the reaction was shown to have reached 100% completion by HPLC peak area. The solution was cooled to room temperature and solvent removed under reduced pressure. Hexane (10 mL) was added to the flask and the precipitated residue collected by filtration and rinsed with hexane to give methyl pyropheophorbide-a (70 mg, 77%).

Workup

  1. temperaturethe mixture was refluxed under argon
  2. customsolvent removed under reduced pressure
  3. additionHexane (10 mL) was added to the flask
  4. filtrationthe precipitated residue collected by filtration
  5. washrinsed with hexane

Sources & evidence

ORD record
ord-2bbfcd26d2ba44f3be2401f5204f07ae
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

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