2,6-Diaminopyridine → HCID 11203277, compound

HRID 1894932Notes

Reaction equation

HRID 1894932 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[C:7]([CH2:11]Br)[C:6]([CH2:13][CH3:14])=[C:5]([CH2:15]Br)[C:4]=1[CH2:17][CH3:18].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[N:21]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[NH2:26][C:22]1[N:21]=[C:20]([NH:19][CH2:2][C:3]2[C:8]([CH2:9][CH3:10])=[C:7]([CH2:11][NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[N:21]=3)[C:6]([CH2:13][CH3:14])=[C:5]([CH2:15][NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[N:21]=3)[C:4]=2[CH2:17][CH3:18])[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 88612,6-DiaminopyridineHCID 11430Potassium CarbonateHCID 45893521,3,5-Tris(bromomethyl)-2,4,6-triethylbenzene

Product 1

HCID 11203277HCID 11203277, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,3,5-tris(bromomethyl)-2,4,6-triethyl-benzene (0.79 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 40%. M.p. 164-165° C.; 1H NMR (500 MHz, CDCl3): δ=1.22 (t, 9H, J=7.5 Hz), 2.75 (q, 6H, J=7.5 Hz), 4.05 (t, 3H, J=4.2 Hz), 4.20 (s, 6H), 4.35 (d, 6H, J=4.2 Hz), 5.83-5.86 (m, 6H), 7.24 (m, 3H); 13C NMR (125 MHz, CDCl3): δ=16.9, 23.0, 40.6, 95.9, 96.9, 133.3, 139.4, 143.8, 157.8, 157.9; HR-MS calcd for C30H39N9: 525.3328; found: 525.3322. Rf=0.21 (CHCl3/CH3OH 7:1 v/v).

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-91ec6f38e2e84871b9a82295dd0e8199
Source dataset
uspto-grants-2013_08
Patent number
US08513420B2

Reaction notes

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