Potassium Carbonate → HCID 59139847, compound

HRID 1624886Notes

Reaction equation

HRID 1624886 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([O:11][CH3:12])=[N:7][N:6]([C:13]2[CH:14]=[C:15]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=2)[C:5]1=[O:23])[CH:2]=[CH2:3].[CH:24]([C:27]1[CH:34]=CC(CBr)=[CH:29][CH:28]=1)([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CCOC(C)=O.O>[CH:24]([C:27]1[CH:28]=[CH:29][C:2]([CH2:1][N:4]2[C:9](=[O:10])[C:8]([O:11][CH3:12])=[N:7][N:6]([C:13]3[CH:14]=[C:15]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=3)[C:5]2=[O:23])=[CH:3][CH:34]=1)([CH3:26])[CH3:25]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 477191-(Bromomethyl)-4-(propan-2-yl)benzeneHCID 68699731HCID 68699731, compound

Product 1

HCID 59139847HCID 59139847, compoundYield 11.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to Scheme 3 Step 5: A suspension of compound 6(D) (60 mg, 0.22 mmol), 4-isopropylbenzyl bromide (41 μL, 0.24 mmol) and potassium carbonate (90 mg, 0.65 mmol) was stirred at 60° C. for 15 h in acetonitrile (2 mL). The mixture was diluted with AcOEt and water. The organic layer was washed twice with water and once with brine. The resulting organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (Merck Flashmart prepacked column 10 g SiO2) using CH2Cl2/MeOH 98/2 as eluent to afford N-(3-(4-(4-isopropylbenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 6(E) (10 mg, 11%) as a yellow solid.

Workup

  1. washThe organic layer was washed twice with water and once with brine
  2. dry with materialThe resulting organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography over silica gel (Merck Flashmart prepacked column 10 g SiO2)

Sources & evidence

ORD record
ord-09de4a7411ce48deb71427bf464eda86
Source dataset
uspto-grants-2014_07
Patent number
US08779129B2

Reaction notes

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