Uracil → HCID 68524223, compound

HRID 884176Notes

Reaction equation

HRID 884176 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C[Si](C)(C)N[Si](C)(C)C.[Cl:18][C:19]1[CH:20]=[C:21]([CH:40]=[CH:41][C:42]=1[Cl:43])[C:22]([NH:24][C:25]1[CH:26]=[N:27][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38]Cl)=[CH:34][CH:33]=2)=[CH:29][CH:30]=1)=[O:23]>[Sn](Cl)(Cl)(Cl)Cl.CO>[Cl:18][C:19]1[CH:20]=[C:21]([CH:40]=[CH:41][C:42]=1[Cl:43])[C:22]([NH:24][C:25]1[CH:26]=[N:27][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][N:1]3[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]3=[O:3])=[CH:34][CH:33]=2)=[CH:29][CH:30]=1)=[O:23]

Participants

6

Reactant 3

HCID 1174UracilHCID 13838HexamethyldisilazaneHCID 68525073HCID 68525073, compound

Product 1

HCID 68524223HCID 68524223, compound

Reagents, catalysts & solvents 2

HCID 24287Tin tetrachlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

To uracil (200 mg, 1.8 mmol) was added hexamethyldisilazane (5 mL), and the resulting solution was stirred for 5.5 hours at 150° C. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was dissolved in a solution of acetonitrile (10 mL)-THF (5 mL), and to this solution were added 3,4-dichloro-N-[6-(4-chloromethylphenoxy)pyridin-3-yl]benzamide (500 mg, 1.2 mmol) and tin tetrachloride (3 drops). The resulting solution was refluxed for 2.5 hours. To this reaction solution was added methanol (1 mL), and the resulting solution was stirred for 30 minutes at room temperature. The resulting reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol:chloroform=1:99→3:97), to thereby yield 20 mg of the title compound.

Workup

  1. customInsoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in a solution of acetonitrile (10 mL)-THF (5 mL)
  4. temperatureThe resulting solution was refluxed for 2.5 hours
  5. stirringthe resulting solution was stirred for 30 minutes at room temperature
  6. customThe resulting reaction solution
  7. concentrationwas concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methanol:chloroform=1:99→3:97)

Sources & evidence

ORD record
ord-8060058e44a540c888815cf8869a6a97
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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