Cesium carbonate → 7-Chloro-2-(2,6-dichlorobenzyl)oxazolo[5,4-d]pyrimidine

HRID 60187

Reaktionsgleichung

Reaktionsgleichung von HRID 60187
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([NH:12][C:13]1[C:14](Cl)=[N:15][CH:16]=[N:17][C:18]=1[Cl:19])=[O:11].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Cl:19][C:18]1[C:13]2[N:12]=[C:10]([CH2:9][C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[O:11][C:14]=2[N:15]=[CH:16][N:17]=1

Komponenten

4

Edukt 2

HCID 10796Cesium carbonateHCID 577424622-(2,6-Dichloro-phenyl)-N-(4,6-dichloro-pyrimidin-5-yl)-acetamide

Produkt 1

HCID 577424567-Chloro-2-(2,6-dichlorobenzyl)oxazolo[5,4-d]pyrimidineAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-(2,6-dichloro-phenyl)-N-(4,6-dichloro-pyrimidin-5-yl)-acetamide (183 mg, 0.52 mmol) in CH3CN (3 mL) was added Cs2CO3 (342 mg, 1.1 mmol). The resulting mixture was heated to 60° C. in a sealed tube. After 2 h, the reaction mixture was cooled and concentrated. The residue was purified by FCC to afford a colorless solid (100 mg, 61%). MS (ESI): mass calcd. for C12H6Cl3N3O, 312.9; m/z found, 313.9 [M+H]+. 1H NMR (CD3OD): 8.69 (s, 1H), 7.43 (d, J=8.0 Hz, 2H), 7.33-7.28 (m, 1H), 4.72 (s, 2H).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. customThe residue was purified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-8062cde3231f435abb78fc753dbae9cf
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440978B2

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