Toluene → 4-Chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine

HRID 611531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611531
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[N+:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([O-:17])=[O:16].C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O.C(O)C>[Cl:1][C:2]1[C:3]2[C:10]([C:21]3[CH:22]=[CH:23][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=3)=[CH:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27735524-Nitrophenylboronic acidHCID 195974264-Chloro-5-iodo-7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 195974814-Chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 4-chloro-5-iodo-7-isopropylpyrrolo[2,3-d]pyrimidine (0.57 g), 4-nitrophenylboronic acid (0.30 g), bis(triphenylphosphine)palladium (II) chloride (0.126 g), toluene (15 ml), ethanol (2 ml), water (4 ml) and sodium bicarbonate (0.45 g) was heated under nitrogen at 105° C. for 8 hours. The mixture was cooled to ambient temperature and then partitioned between brine (50 ml) and ethyl acetate (50 ml). The aqueous layer was further extracted with ethyl acetate and the combined ethyl acetate extracts were washed with water, dried, filtered and evaporated to leave a solid which was purified by flash column chromatography on silica using cyclohexane with increasing amounts of ethyl acetate as the mobile phase to give 4-chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine.

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between brine (50 ml) and ethyl acetate (50 ml)
  3. extractionThe aqueous layer was further extracted with ethyl acetate
  4. washthe combined ethyl acetate extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a solid which
  9. customwas purified by flash column chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-e4bd162e3c0b4c23a0239173e397c33f
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06001839

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