HCID 21713226, compound → 5-Ethenyl-4,6-dimethylpyridin-2-amine

HRID 1740944Notes

Reaction equation

HRID 1740944 reaction equation
CBr.[C:3]1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].[CH:28]([C:30]1[C:31]([CH3:38])=[CH:32][C:33]([NH2:37])=[N:34][C:35]=1[CH3:36])=O>C1COCC1>[CH3:38][C:31]1[C:30]([CH:28]=[CH2:3])=[C:35]([CH3:36])[N:34]=[C:33]([NH2:37])[CH:32]=1

Participants

5

Reactant 3

HCID 21713226HCID 21713226, compoundHCID 21834435HCID 21834435, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 218344475-Ethenyl-4,6-dimethylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 10 mL round bottomed flask was added a magnetic stirrer bar, 500 mg (1.2 mmol) of triphenylphosphonium methyl bromide and 137 mg (1.22 mmol) of potassium t-butoxide. The flask is stoppered with a rubber septum, flushed with nitrogen and 5 mL of dry THF was added to the mixture. After stirring at room temperature for 1 h, the solution was cooled to -60° C. and a solution of 170 mg (1.0 mmol) of 5-formyl4,6-dimethyl-2-aminopyridine in 2 mL of THF was added. After stirring for 30 minutes, the solution was warmed to 25° C. and stirred for 1 h. The solvent was removed in vacuo and and the title compound purified by silica gel column chromatography eluted with (methylene chloride/methanol (95:5).

Workup

  1. additionIn a 10 mL round bottomed flask was added a magnetic stirrer bar
  2. customflushed with nitrogen and 5 mL of dry THF
  3. additionwas added to the mixture
  4. temperaturethe solution was cooled to -60° C.
  5. stirringAfter stirring for 30 minutes
  6. temperaturethe solution was warmed to 25° C.
  7. stirringstirred for 1 h
  8. customThe solvent was removed in vacuo
  9. customthe title compound purified by silica gel column chromatography
  10. washeluted with (methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-c10a673c35f94934898e31ba5ea9cf98
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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