2,6-Diaminopyridine → HCID 86641414, compound

HRID 1894931Notes

Reaction equation

HRID 1894931 reaction equation
Br[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([CH2:10]Br)[C:6]([CH3:12])=[C:5]([CH2:13]Br)[C:4]=1[CH3:15].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[N:18]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[NH2:23][C:19]1[N:18]=[C:17]([NH:16][CH2:2][C:3]2[C:8]([CH3:9])=[C:7]([CH2:10][NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[N:18]=3)[C:6]([CH3:12])=[C:5]([CH2:13][NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[N:18]=3)[C:4]=2[CH3:15])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 88612,6-DiaminopyridineHCID 11430Potassium CarbonateHCID 891402,4,6-Tris(bromomethyl)mesitylene

Product 1

HCID 86641414HCID 86641414, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,3,5-tris(bromomethyl)-2,4,6-trimethyl-benzene (0.72 g, 1.8 mmol), 2,6-diamino-pyridine (1.20 g, 11 mmol), and K2CO3 (0.79 g) in CH3CN (100 mL) was stirred at room temperature for 24 h and then heated under reflux for 2 h. After filtration of the reaction mixture and evaporation of CH3CN, the obtained powder was suspended in CHCl3. The suspension was filtrated, the chloroform solution was washed several times with water, dried, and the solvent was removed under reduced pressure. The crude product was crystallized from THF/hexane. Yield 60%. M.p. 130-132° C.; 1H NMR (500 MHz, CDCl3): δ=2.38 (s, 9H), 4.01 (t, 3H, J=4.4 Hz), 4.15 (s, 6H), 4.35 (d, 6H, J=4.4 Hz), 5.81-5.84 (m, 6H), 7.24 (d, 3H). 13C NMR (125 MHz, CDCl3): δ=15.83, 41.65, 95.70, 96.81, 133.78, 136.84, 139.25, 157.68, 157.99. HR-MS calcd for C27H33N9: 483.2859; found: 483.2867.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. filtrationAfter filtration of the reaction mixture and evaporation of CH3CN
  4. filtrationThe suspension was filtrated
  5. washthe chloroform solution was washed several times with water
  6. customdried
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was crystallized from THF/hexane

Sources & evidence

ORD record
ord-7a5568b86ee5470e9548220aef27d3ce
Source dataset
uspto-grants-2013_08
Patent number
US08513420B2

Reaction notes

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