Sodium Carbonate → HCID 68851418, compound

HRID 1786120Notes

Reaction equation

HRID 1786120 reaction equation
[CH2:1]([C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([S:12][CH3:13])[N:6]=1)[CH2:2][CH:3]=[CH2:4].[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:5]1[CH:10]=[C:9]([C:15]2[O:14][CH:18]=[CH:17][CH:16]=2)[N:8]=[C:7]([S:12][CH3:13])[N:6]=1)[CH2:2][CH:3]=[CH2:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 86032208HCID 86032208, compound

Product 1

HCID 68851418HCID 68851418, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-(3-buten-1-yl)-6-chloro-2-(methylthio)-pyrimidine (0.79 g, 3.69 mmol), 2-furanylboronic acid (0.45 g, 4.06 mmol), aq. Na2CO3 solution (2M, 4.1 mL) in dioxane (37 mL) at room temperature was added tetrakis(triphenylphosphine)palladium(0) (0.21 g, 0.185 mmol). The reaction mixture in sealed tube was stirred and refluxed at 110° C. for 18 hours. After the reaction was completed, the mixture was filtered through a pad of silica gel. The filtrate was evaporated in vacuo. The residue was dissolved in methylene chloride (30 mL). It was washed with water (30 mL×2). The organic layer was dried over MgSO4 and filtered, evaporated in vacuo. The residue was purified by column chromatography to provide the title compound. MH+247.

Workup

  1. filtrationthe mixture was filtered through a pad of silica gel
  2. customThe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride (30 mL)
  4. washIt was washed with water (30 mL×2)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1a6e6ce0e3514389981a3e1f29dc1e72
Source dataset
uspto-grants-2009_03
Patent number
US07507726B2

Reaction notes

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