Cesium carbonate → N-(4-(trifluoromethyl)phenyl)-4-vinyl-1,3,5-triazin-2-amine

HRID 77476Notes

Reaction equation

HRID 77476 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:3]=1.[CH:19](B1OB(C=C)OB(C=C)O1)=[CH2:20].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:16][C:15]([F:18])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:4]2[N:3]=[C:2]([CH:19]=[CH2:20])[N:7]=[CH:6][N:5]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 2734807TrivinylboroxinHCID 860496674-chloro-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine

Product 1

HCID 86679766N-(4-(trifluoromethyl)phenyl)-4-vinyl-1,3,5-triazin-2-amineYield 16.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine (0.5 g, 1.821 mmol) in dioxane (8 mL) and water (2 mL) were added trivinylboroxin (0.588 g, 3.64 mmol), cesium carbonate (1.780 g, 5.46 mmol). The reaction mixture was flushed with nitrogen for 10 min and Tetrakis (0.210 g, 0.182 mmol) was added. The reaction mixture was heated at 90° C. for 2 h then filtered through a pad of celite and washed with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel using 15% ethyl acetate in hexane to give N-(4-(trifluoromethyl)phenyl)-4-vinyl-1,3,5-triazin-2-amine as a white solid (0.08 g, 12.21% yield). LCMS: R.T.=1.14 min; [M+H]+=267.1.

Workup

  1. customThe reaction mixture was flushed with nitrogen for 10 min
  2. filtrationthen filtered through a pad of celite
  3. washwashed with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel using 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-96ca640b9c8c4eecbd011e645062e390
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

Loading…