Dimethylformamide → HCID 66803229, compound

HRID 341475Notes

Reaction equation

HRID 341475 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.[C:19](=O)([O-])[O-].[K+].[K+].CI.CN(C=O)C>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[N:5]=[C:4]([N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[CH3:19])[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 668026572-Amino-4 cyano-6-(2,3-difluorophenylamino)-[1,3,5]triazine2×

Product 1

HCID 66803229HCID 66803229, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 311Citric AcidSolvent

Procedure

To 2-amino-4 cyano-6-(2,3-difluorophenylamino)-[1,3,5]triazine (Intermediate 54, 332 mg, 1.34 mmol) were added potassium carbonate (203 mg, 1.46 mmol), methyl iodide (83 μL, 1.34 mmol) and anhydrous DMF (3 mL). The mixture was stirred at room temperature for 1 h and then diluted with 1M aq. citric acid (10 mL). The resulting mixture was extracted with ethyl acetate (2×10 mL) and the combined extracts washed with water (4×10 mL), saturated brine (10 mL) and dried further over anhydrous sodium sulfate. Evaporation of the solvent gave a gum which was loaded onto a silica column and eluted with heptane-30% ethyl acetate to give the desired compound (320 mg, 91%). Method B HPLC-MS: MH+ requires m/z=262. Found: m/z=262, Rt=1.76 min (98%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×10 mL)
  2. washthe combined extracts washed with water (4×10 mL), saturated brine (10 mL)
  3. dry with materialdried further over anhydrous sodium sulfate
  4. customEvaporation of the solvent
  5. customgave a gum which
  6. washeluted with heptane-30% ethyl acetate

Sources & evidence

ORD record
ord-c73e723ebd5a40fea007c3751dbc7dec
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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