Dimethylformamide → HCID 86720754, compound

HRID 2167706Notes

Reaction equation

HRID 2167706 reaction equation
CN(C)C=O.Br[C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[N:11][CH:12]=1.C([Sn](CCCC)(CCCC)[C:19]([O:21][CH2:22][CH3:23])=[CH2:20])CCC.[F-].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[CH2:22]([O:21][C:19]([C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[N:11][CH:12]=1)=[CH2:20])[CH3:23]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 143877445-Bromo-2-methylpyrimidine

Product 1

HCID 86720754HCID 86720754, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To a N,N-dimethylformamide (10 mL) solution of 5-bromo-2-methylpyrimidine (0.50 g), tributyl(1-ethoxyethenyl)stannane (1.5 g) and bis(triphenylphosphine)palladium(II) dichloride (0.14 g) were added, and the resultant was stirred at 100° C. for 1 hour. After standing to cool to room temperature, an aqueous potassium fluoride solution (20 mL) and diethyl ether (20 mL) were added to the reaction solution, and the resultant was stirred. Insoluble material was filtered off through Celite, and the filtrate was subjected to extraction with diethyl ether. The organic layer was dried over magnesium sulfate, and the desiccant was filtered off. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=90/10→75/25) to obtain the title compound (0.48 g) as a pale yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. stirringthe resultant was stirred
  3. filtrationInsoluble material was filtered off through Celite
  4. extractionthe filtrate was subjected to extraction with diethyl ether
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationthe desiccant was filtered off
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=90/10→75/25)

Sources & evidence

ORD record
ord-cba4065e15f64119a043bca2310243e4
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

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