Potassium Cyanide → 4-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazine-2-carbonitrile

HRID 341466Notes

Reaction equation

HRID 341466 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([NH2:16])[N:3]=1.[C-:17]#[N:18].[K+]>CN(C=O)C.CCOC(C)=O>[NH2:16][C:4]1[N:5]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:7]=[C:2]([C:17]#[N:18])[N:3]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 807666266-chloro-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamine2×

Product 1

HCID 668029964-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazine-2-carbonitrileYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 6-chloro-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamine (Intermediate 41, 360 mg, 2.67 mmol) in DMF (25 ml) was added potassium cyanide (435 mg, 6.68 mmol). The reaction was stirred at 120 C under nitrogen for 2 h. The reaction mixture was diluted with EtOAc (80 ml); the solution was then extracted with 5% aq. sodium hydrogencarbonate solution (2×20 mL), and saturated brine (2×5 mL). After evaporation of the solvent, the crude residue was purified by FCC over silica gel eluting with heptane:EtOAc 1:0 to 8:2 to 6:4 to furnish the desired product (380 mg, 63%). Method C HPLC-MS: MH+ requires m/z=227. Found: m/z=227, Rt=1.24 min (95%).

Workup

  1. extractionthe solution was then extracted with 5% aq. sodium hydrogencarbonate solution (2×20 mL), and saturated brine (2×5 mL)
  2. customAfter evaporation of the solvent
  3. customthe crude residue was purified by FCC over silica gel eluting with heptane:EtOAc 1:0 to 8:2 to 6:4

Sources & evidence

ORD record
ord-4ffb1dccb8854e4ea18e4ad5610b7e92
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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