Water → N,N'-diphenyl-N''-(4-pyridylmethyl)-1,3,5-triazine-2,4,6-triamine

HRID 2223824Notes

Reaction equation

HRID 2223824 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C.O>C(#N)C>[C:16]1([NH:15][C:4]2[N:5]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:7]=[C:2]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[N:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 160881,3,5-Triazine-2,4-diamine, 6-chloro-N2,N4-diphenyl-HCID 773174-PyridinemethanamineHCID 81531Diisopropylethylamine

Product 1

HCID 10150345N,N'-diphenyl-N''-(4-pyridylmethyl)-1,3,5-triazine-2,4,6-triamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A 200 mg portion of 6-chloro-N,N′-diphenyl-1,3,5-triazine-2,4-diamine was dissolved in 10.0 ml of acetonitrile, and 145 mg of 4-(aminomethyl)pyridine and 0.585 ml of diisopropylethylamine were added thereto and stirred overnight at 80° C. The reaction solution was cooled down to room temperature, and then mixed with water and extracted with chloroform. The organic layer was washed with 5% citric acid and saturated brine and then dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, the thus obtained residue was applied to a silica gel column chromatography and eluted with ethyl acetate:n-hexane (2:1), and then the thus obtained crude product was crystallized from ethyl acetate/n-hexane, thereby obtaining 107 mg of N,N′-diphenyl-N″-(4-pyridylmethyl)-1,3,5-triazine-2,4,6-triamine as light red crystals.

Workup

  1. temperatureThe reaction solution was cooled down to room temperature
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with 5% citric acid and saturated brine
  4. customdried
  5. customThe solvent was evaporated under a reduced pressure
  6. washeluted with ethyl acetate:n-hexane (2:1)
  7. customthe thus obtained crude product
  8. customwas crystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-0567f529f8734978bf303f29f1f859c5
Source dataset
uspto-grants-2008_05
Patent number
US07375222B2

Reaction notes

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