Potassium Carbonate → HCID 59139847, compound

HRID 1799464Notes

Reaction equation

HRID 1799464 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-2c9a74f781b4414980f9c02ebcd1d216
Source dataset
uspto-grants-2013_01
Patent number
US08344138B2

Reaction notes

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