2-Amino-6-methylpyridine → 6-Methyl-N-(6-methyl-2-pyridyl)pyridin-2-amine

HRID 2113392Notes

Reaction equation

HRID 2113392 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.Br[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[CH3:8][C:4]1[N:3]=[C:2]([NH:1][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 157652-Amino-6-methylpyridineHCID 792052-Bromo-6-methylpyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 30210056-Methyl-N-(6-methyl-2-pyridyl)pyridin-2-amineYield 57.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask were added 3.1 g of 2-amino-6-methylpyridine, 5.0 g of 2-bromo-6-methylpyridine, 3.6 g of sodium tert-butoxide, and 150 ml toluene. The mixture was purged thoroughly with nitrogen and 160 mg of 1,1′-bis(diphenylphosphino)ferrocene and 65 mg of palladium acetate were added. The reaction mixture was heated to 80 C for 3 hours, and then cooled to 22 C. After quenching with 100 ml of water, the product was extracted with 75 ml ethyl acetate. The product was extracted with 75 ml of 1M hydrochloric acid, and then basified with 3M sodium hydroxide. Following extraction with 75 ml of ethyl acetate and washing with 30 ml of water, the solvent was removed. The product was purified by dissolving in a minimum amount of hot 2-propanol, and after cooling to 5 C, the product was filtered, washed with cold 2-propanol, and dried, resulting in 3.3 g of a tan solid.

Workup

  1. customThe mixture was purged thoroughly with nitrogen and 160 mg of 1,1′-bis(diphenylphosphino)ferrocene and 65 mg of palladium acetate
  2. additionwere added
  3. temperatureThe reaction mixture was heated to 80 C for 3 hours
  4. temperaturecooled to 22 C
  5. customAfter quenching with 100 ml of water
  6. extractionthe product was extracted with 75 ml ethyl acetate
  7. extractionThe product was extracted with 75 ml of 1M hydrochloric acid
  8. extractionextraction with 75 ml of ethyl acetate
  9. washwashing with 30 ml of water
  10. customthe solvent was removed
  11. customThe product was purified
  12. dissolutionby dissolving in a minimum amount of hot 2-propanol
  13. temperatureafter cooling to 5 C
  14. filtrationthe product was filtered
  15. washwashed with cold 2-propanol
  16. customdried

Sources & evidence

ORD record
ord-ad65f97ca8d54322a2ffb3c6647d85f0
Source dataset
uspto-grants-2009_04
Patent number
US07525717B2

Reaction notes

Loading…