Sodium Carbonate → 6-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrile

HRID 12707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12707
I[C:2]1[C:3]([O:10][CH3:11])=[N:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12]([C:14]1[N:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=[CH:16][CH:15]=1)#[N:13].C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:9][O:8][C:5]1[N:4]=[C:3]([O:10][CH3:11])[C:2]([C:18]2[N:19]=[C:14]([C:12]#[N:13])[CH:15]=[CH:16][CH:17]=2)=[CH:7][N:6]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2634165-Iodo-2,4-dimethoxypyrimidineHCID 177504686-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile

Produkt 1

HCID 589942216-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrileAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

5-Iodo-2,4-dimethoxy-pyrimidine (500 mg, 1.88 mmol) was dissolved in degassed n-PrOH (40 ml) and then 6-cyano-pyridine-2-boronic acid pinacol ester (650 mg, 2.82 mmol), Na2CO3 (598 mg, 5.64 mmol), PPh3 (164 mg, 0.62 mmol) and Pd(OAc)2 (42 mg, 0.19 mmol) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPrOH to give 200 mg of the title compound (44% yield).

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. customThe solvent was evaporated
  3. customthe crude was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was triturated with iPrOH

Quellen und Nachweise

ORD-Eintrag
ord-9c661d50fd2d4b33b0dcf9a476560655
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

Notizen zur Reaktion

Wird geladen…