Sodium Carbonate → 5-(2-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

HRID 12718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12718
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](I)=[CH:5][N:4]=1.[Cl:12][C:13]1[C:18](B(O)O)=[CH:17][CH:16]=[CH:15][N:14]=1.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]>[Cl:12][C:13]1[C:18]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)=[CH:17][CH:16]=[CH:15][N:14]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2634165-Iodo-2,4-dimethoxypyrimidineHCID 2762704(2-Chloropyridin-3-yl)boronic acid

Produkt 1

HCID 589942445-(2-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

2,4-Dimethoxy-5-iodo-pyrimidine (1 g, 3.76 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-chloropyridine-3-boronic acid (882 mg, 5.61 mmol), Na2CO3 (800 mg, 7.6 mmol), PPh3 (98 mg, 0.37 mmol) and Pd(OAc)2 (40 mg, 0.19 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated to give the title compound that was used without further purification in the next step (quantitative yield).

Aufarbeitung

  1. temperatureat reflux for 4 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-39e094d93f7f4d7f97b94ae4898ea550
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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