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Sodium Carbonate → 9-isopropyl-6-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-9H-purine

HRID 1518332
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1518332
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]([CH3:13])[CH3:12].[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:11]([N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[C:24]1[CH:25]=[CH:26][C:21]([O:20][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)=[CH:22][CH:23]=1)([CH3:13])[CH3:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 4146346-Chloro-9-isopropyl-9H-purineHCID 50176524-(Tetrahydro-2H-pyran-2-yloxy)phenylboronic Acid (contains varying amounts of Anhydride)

Produkt 1

HCID 594476359-isopropyl-6-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-9H-purine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Compound 52B (165 mg, 0.84 mmol) in toluene (5 ml) was treated sequentially with 4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid (280 mg, 1.26 mmol), tetrakis(triphenylphosphine)palladium(0) (48.6 mg, 0.042 mmol) and sodium carbonate (2N aq.) (1.26 ml, 2.52 mmol). The reaction vessel was purged with nitrogen and heated at reflux overnight. The reaction mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel eluting with a gradient of 0 to 5% MeOH in CH2Cl2: 1H NMR (300 MHz, DMSO-d6) δ ppm 8.92 (1H, s), 8.83 (2H, m), 8.74 (1H, s), 7.22 (2H, m), 5.63 (1H, t), 4.92 (1H, septet), 3.79 (1H, ddd), 3.60 (1H, m), 1.82 (4H, m), 1.60 (6H, d), 1.55 (2H, m).

Aufarbeitung

  1. customThe reaction vessel was purged with nitrogen
  2. temperatureheated
  3. temperatureat reflux overnight
  4. additiondiluted with EtOAc
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by column chromatography on silica gel eluting with a gradient of 0 to 5% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-6b47d4906c4644d9973b8e1386945d0b
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08232273B2

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