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Potassium Phosphate, Tribasic → HCID 136368403, Verbindung

HRID 2100559
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2100559
Br[C:2]1[CH:22]=[N:21][C:5]2[N:6]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[CH:23]1(B(O)O)[CH2:25][CH2:24]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[CH:23]1([C:2]2[CH:22]=[N:21][C:5]3[N:6]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[NH:8][C:9](=[O:10])[C:4]=3[CH:3]=2)[CH2:25][CH2:24]1
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Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 135899296HCID 135899296, Verbindung

Produkt 1

HCID 136368403HCID 136368403, VerbindungAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845
palladium(II) acetate
Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Palladium(II) acetate (1 mg, 4.5 μmol) was added to a degassed suspension of 6-bromo-2-(4-phenyl-butyl)-3H-pyrido[2,3-d]pyrimidin-4-one (20 mg, 55 μmol; example 26), cyclopropyl boronic acid (10 mg, 110 μmol), potassium phosphate (59 mg, 275 μmol) and tricyclohexylphosphine (3 mg, 9 μmol) in toluene (360 μl) and water (24 μl) under an argon atmosphere. The reaction mixture was heated for 14 h to 100° C. and poured onto ice cold isopropyl acetate/brine 1/1. The layers were separated, the aqueous layer was extracted two times with isopropyl acetate, the combined extracts were washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure left a yellow solid which was purified by preparative thin layer chromatography (silica gel, isopropyl acetate/heptane) to give 6-cyclopropyl-2-(4-phenyl-butyl)-3H-pyrido[2,3-d]pyrimidin-4-one (1 mg, 3.1 μmol; 6%) as yellow crystals. MS: m/e=320.2 [M+H+].

Aufarbeitung

  1. temperatureThe reaction mixture was heated for 14 h to 100° C.
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted two times with isopropyl acetate
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent under reduced pressure
  7. waitleft a yellow solid which
  8. customwas purified by preparative thin layer chromatography (silica gel, isopropyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-6ee95202bfaa43138ac4617bc30e2f9b
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07572801B2

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