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2,2'-Bipyridine → HCID 86696636, Verbindung

HRID 1468620
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1468620
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.[NH2:7][C:8]1[N:16]=[C:15]2[C:11]([NH:12][C:13](=[O:20])[N:14]2[CH2:17][CH2:18][OH:19])=[C:10]([Cl:21])[N:9]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CN=C(C2C=CC=CN=2)C=1.[NH4+].[Cl-]>ClC(Cl)C.CN(C)C=O.CC([O-])=O.CC([O-])=O.[Cu+2].O>[NH2:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]([CH:1]3[CH2:3][CH2:2]3)[C:13](=[O:20])[N:14]2[CH2:17][CH2:18][OH:19])=[C:10]([Cl:21])[N:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 5

HCID 14742,2'-BipyridineHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 2760897Cyclopropylboronic acidHCID 86696631HCID 86696631, Verbindung

Produkt 1

HCID 86696636HCID 86696636, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 8895Cupric acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of cyclopropylboronic acid (0.369 g, 44 mmol), 2-amino-6-chloro-9-(2-hydroxyethyl)-7H-purin-8-one (5 g, 22 mmol) and Na2CO3 (0.462 g, 44 mmol) were taken in dichloroethane (20 ml) and dimethylformamide (10 ml). A suspension of Cu(OAc)2 (0.399 g, 22 mmol) and bipyridine (0.343 g, 22 mmol) in hot dichloroethane (30 ml) was added to the above mixture. The mixture was stirred at 70° C. for 18 hours under air. The resulting mixture was cooled to room temperature, and a saturated aqueous NH4Cl solution was added, followed by water. The organic layer was separated and the aqueous layer was extracted three times with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to get crude 2-amino-6-chloro-7-cyclopropyl-9-(2-hydroxyethyl)purin-8-one (1.6 g, 27%) as an off white solid. 1HNMR (400 MHz, DMSO d6): δ 0.97-1.02 (m, 4H); 2.89-2.92 (m, 1H); 3.61-3.67 (m, 2H); 3.71-3.74 (m, 2H); 4.83 (t, J=12.8 Hz, 1H); 6.67 (bs, 2H)

Aufarbeitung

  1. additionwas added to the above mixture
  2. temperatureThe resulting mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with DCM
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-10bb719efafc4c3398d8d5c96ddcbcdf
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09006177B2

Notizen zur Reaktion

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