Cesium carbonate → 5-{1-tert-Butyl-2-[2-(2,4-dimethyl-oxazol-5-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine

HRID 1966752

Reaktionsgleichung

Reaktionsgleichung von HRID 1966752
[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1I)([CH3:4])([CH3:3])[CH3:2].[CH3:28][C:29]1[O:30][CH:31]=[C:32]([CH3:34])[N:33]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:31]1[O:30][C:29]([CH3:28])=[N:33][C:32]=1[CH3:34])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 1389612,4-DimethyloxazoleHCID 585420695-[1-tert-butyl-2-(2-iodo-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

Produkt 1

HCID 585419305-{1-tert-Butyl-2-[2-(2,4-dimethyl-oxazol-5-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a vial are added 5-[1-tert-butyl-2-(2-iodo-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (50 mg, 0.107 mmol), 2,4-dimethyl-oxazole (21 mg, 0.216 mol), palladium(II) acetate (5 mg, 0.022 mmol), PPh3 (6 mg, 0.023 mmol) and Cs2CO3 (70 mg, 0.215 mmol) in DMF (1.5 mL). The reaction mixture is stirred at 140° C. for 18 hours. The reaction mixture is diluted with EtOAc/water. The organic layer is separated, washed with brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 0-5% MeOH/CH2Cl2 as the eluent. The product fractions are collected and concentrated to afford the title compound (19 mg, 41%) as an off-white solid. LCMS (ESMS): m/z 439.86 (M++1)

Aufarbeitung

  1. customThe organic layer is separated
  2. washwashed with brine
  3. customdried under anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel flash column chromatography with 0-5% MeOH/CH2Cl2 as the eluent
  7. customThe product fractions are collected
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c897844a27c649219e060d5138cf8e00
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420655B2

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