Potassium Cyanide → 2-(2-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetonitrile

HRID 1624916Notes

Reaction equation

HRID 1624916 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([O:14][CH3:15])=[N:10][N:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:22]Br)[C:8]2=[O:24])=[CH:4][CH:3]=1.[C-:27]#[N:28].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([O:14][CH3:15])=[N:10][N:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:22][C:27]#[N:28])[C:8]2=[O:24])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 686977962-(2-(bromomethyl)phenyl)-4-(4-chlorobenzyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 251062892-(2-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetonitrileYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

According to Scheme 9 Step 2: A mixture of 4-(4-chlorobenzyl)-2-(2-(bromomethyl)phenyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione (70 mg, 0.16 mmol) in DMF (2 mL) and potassium cyanide (31 mg, 0.13 mmol) was stirred at 20° C. 12 hours. The reaction mixture was quenched with water and extracted with ethyl acetate (×3). The combined organic layers were successively washed with water, brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography, 10 g prepacked column, DCM/MeOH 99/1 to afford 2-(2-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetonitrile 4.167 (50 mg, Yield=81%) as a white oil.

Workup

  1. custom12 hours
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic layers were successively washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography, 10 g

Sources & evidence

ORD record
ord-a87e5f2039d64fd792f4eb20d0deb469
Source dataset
uspto-grants-2014_07
Patent number
US08779129B2

Reaction notes

Loading…