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

HRID 341465Notes

Reaction equation

HRID 341465 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([C:9]#[N:10])[N:3]=1.CN(C=O)C.C(N(C(C)C)CC)(C)C.[CH3:25][NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCOC(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([N:26]([CH3:25])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:5]=[C:4]([C:9]#[N:10])[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7515N-MethylanilineHCID 81531DiisopropylethylamineHCID 867105172-Amino-4-chloro-6-cyano-[1,3,5]triazine2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2-amino-4-chloro-6-cyano-[1,3,5]triazine (Intermediate 3, 243 mg, 1.6 mmol) was added anhydrous DMF (5 mL), diisopropylethylamine (0.54 mL, 3.1 mmol) and N-methyl-aniline (184 mg, 1.7 mmol). The mixture was heated at 90 C in a pressure tube for 18 h before allowing to cool to room temperature. The reaction mixture was diluted with EtOAc (20 mL), washed with water (2×10 mL) and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to furnish the desired product which was used directly without further purification (138 mg, 39%). Method C HPLC-MS: MH+ requires m/z=227. Found: m/z=227, Rt=1.20 min (93%).

Workup

  1. temperatureThe mixture was heated at 90 C in a pressure tube for 18 h
  2. washwashed with water (2×10 mL)
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e434bc8b4cc0453eae357821b917b963
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

Loading…