Dimethyl Sulfoxide → 4-Cyano-N-methyl-N-3-methylphenyl-[1,3,5]triazine-2,6-diamine
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([C:9]#[N:10])[N:3]=1.CS(C)=O.C(N(C(C)C)CC)(C)C.[CH3:24][NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=1>C(OCC)(=O)C>[C:9]([C:4]1[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([N:25]([CH3:24])[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)[N:5]=1)#[N:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To 2-amino-4-chloro-6-cyano-[1,3,5]triazine (Prepared in an analogous way to Intermediate 3, 46 mg, 296 μmol) was added 1 mL anhydrous DMSO, diisopropylethylamine (77 μL, 444 μmol) and N-methyl-m-toluidine (40 mg, 326 μmol). The mixture was heated at 90 C for 2 h, allowed to cool and diluted with 10 mL ethyl acetate. The mixture was then extracted with water (10 mL), 0.5 M HCl (3×10 mL), water (10 mL) and saturated brine (10 mL). The organic layer was dried further over anhydrous sodium sulfate and evaporated to give the desired product which was used directly without further purification or characterization (42 mg, 59%).
Workup
- temperatureThe mixture was heated at 90 C for 2 h
- temperatureto cool
- extractionThe mixture was then extracted with water (10 mL), 0.5 M HCl (3×10 mL), water (10 mL) and saturated brine (10 mL)
- dry with materialThe organic layer was dried further over anhydrous sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-a4ad9bd160634c66bbeb68c7ef26c5cc
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895733B2
Reaction notes
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