Diethyl Ether → HCID 86762585, compound

HRID 2401208Notes

Reaction equation

HRID 2401208 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:15]([O:17][CH2:18][CH3:19])=[CH2:16])CCC.[F-].[K+].C(OCC)C>CN(C)C=O.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>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[CH2:16])[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 8188604,6-Dichloro-5-methylpyrimidine

Product 1

HCID 86762585HCID 86762585, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4,6-Dichloro-5-methylpyrimidine (2.0 g, 12.27 mmol), bis(triphenylphosphine)palladium(II) chloride (0.172 g, 0.245 mmol) and tributyl[1-(ethyloxy)ethenyl]stannane (4.48 ml, 13.25 mmol) were added together in N,N-dimethylformamide (DMF) (45.8 ml) and the resulting mixture was heated at 80° C. under argon for 18 hours. The reaction mixture was allowed to cool to room temperature and poured into an aqueous solution of potassium fluoride (10.4 g in 104 ml water). Diethyl ether (146 ml) was added and the solid was filtered, washed with diethyl ether (×2) and discarded. The filtrate was separated and the organic layer was washed with water, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by SP4 Biotage column chromatography eluting with a gradient of 0-20% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a yellow oil (1.49 g);

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe solid was filtered
  3. washwashed with diethyl ether (×2)
  4. customThe filtrate was separated
  5. washthe organic layer was washed with water
  6. customdried under magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by SP4 Biotage column chromatography
  9. washeluting with a gradient of 0-20% ethyl acetate and iso-hexane
  10. additionProduct containing fractions
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-406f92cc80ac4acb8fbec2d6b733c92f
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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