Phosphorus oxychloride → 3,3'-(2-Chloropyrimidine-4,6-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane)

HRID 75425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75425
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:14]=[C:13]([N:15]3[CH2:21][CH:20]4[O:22][CH:17]([CH2:18][CH2:19]4)[CH2:16]3)[N:12]=[C:11](O)[N:10]=1)[CH2:2]2.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:11]1[N:10]=[C:9]([N:3]2[CH2:4][CH:5]3[O:8][CH:1]([CH2:7][CH2:6]3)[CH2:2]2)[CH:14]=[C:13]([N:15]2[CH2:21][CH:20]3[O:22][CH:17]([CH2:18][CH2:19]3)[CH2:16]2)[N:12]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178517877HCID 178517877, Verbindung

Produkt 1

HCID 866658883,3'-(2-Chloropyrimidine-4,6-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane)Ausbeute 93 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 25 mL round-bottomed flask was placed 4,6-di(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-ol (27), 12 mg, 0.038 mmol) in POCl3 (3 ml) to give a yellow solution. The mixture was stirred at 100° C. for 4 h. The mixture was cool to room temperature, poured on ice, and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered and concentrated to give the title compound as a white crystalline solid (12 mg, 93%).

Aufarbeitung

  1. customIn a 25 mL round-bottomed flask was placed
  2. temperatureThe mixture was cool to room temperature
  3. additionpoured on ice
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4efd0c7fad3648f0a27c02c0fdeebb29
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835429B2

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