Sodium Carbonate → HCID 58742226, Verbindung

HRID 1514440

Reaktionsgleichung

Reaktionsgleichung von HRID 1514440
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[CH3:10][C:11]1[S:12][C:13](B2OC(C)(C)C(C)(C)O2)=[C:14]([CH3:16])[N:15]=1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][C:11]1[S:12][C:13]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)=[C:14]([CH3:16])[N:15]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 38589014-Iodo-2-(methylthio)pyrimidine2×HCID 185257002,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole

Produkt 1

HCID 58742226HCID 58742226, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

To a solution of 4-iodo-2-methylsulfanyl-pyrimidine (390 mg, 1.56 mmol), 2,4-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiazole (633 mg, 2.65 mmol added portionwise), Na2CO3 (215 mg, 2.02 mmol), triphenylphosphine (42 mg, 0.15 mmol) in nPrOH (25 ml), Pd(OAc)2 (11 mg, 0.047 mmol) was added and the mixture was refluxed for 2 hour. The solvent was evaporated under vacuum, and the crude was dissolved in DCM and washed with water. The organic phase was dried (Na2SO4) and evaporated. A second batch of this compound was prepared according to the same protocol starting from 0.39 mmol of 4-iodo-2-methylsulfanyl-pyrimidine. The residues, deriving from the two batches, were purified by flash chromatography with hexane-ethyl acetate to give the title compound (352, 76% yield).

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was refluxed for 2 hour
  3. customThe solvent was evaporated under vacuum
  4. dissolutionthe crude was dissolved in DCM
  5. washwashed with water
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. customevaporated
  8. customA second batch of this compound was prepared
  9. customwere purified by flash chromatography with hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f1720cfc27794da78a3db6a7e7f88397
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222266B2

Verknüpfte Notizen

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