Tin tetrachloride → HCID 118294255, Verbindung

HRID 2205181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205181
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][NH:5][C:4](=[O:9])[N:3]=1.C(O[CH:14]1[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@:16]([CH2:34][O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([CH:31]([F:33])[F:32])[O:15]1)(=O)C.Cl[Sn](Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>CC#N>[C:20]([O:19][C@@H:18]1[C@H:17]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@:16]([CH2:34][O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH:31]([F:32])[F:33])[O:15][C@H:14]1[N:5]1[CH:6]=[C:7]([Cl:8])[C:2]([NH2:1])=[N:3][C:4]1=[O:9])(=[O:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 131735802HCID 131735802, VerbindungHCID 178509020HCID 178509020, Verbindung

Produkt 1

HCID 118294255HCID 118294255, VerbindungAusbeute 37,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 4-amino-5-chloropyrimidin-2(1H)-one 28 (0.336 g, 2.33 mmol) in anhydrous CH3CN (10 mL) was added BSA (0.945 g, 4.64 mmol) portion-wise while maintaining the reaction temperature at 25° C. After the reaction mixture became clear, compound 5 (0.54 g, 1.16 mmol) in CH3CN (2 mL) and SnCl4 (1.2 g, 4.64 mmol) was added into the mixture. The mixture was stirred at 65° C. for 1 h, then cooled and poured into saturated NaHCO3 solution (20 mL). The organic phase was extracted with ethyl acetate, washed with water, brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. Purification by flash silica gel chromatography [dichloromethane:methanol (40:1)] gave 29 as a white solid (0.24 g, 31%). LC-MS: (M+H)+=550.1

Aufarbeitung

  1. temperaturecooled
  2. extractionThe organic phase was extracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness under reduced pressure
  6. customPurification by flash silica gel chromatography [dichloromethane:methanol (40:1)]

Quellen und Nachweise

ORD-Eintrag
ord-51ae9e32612e44d198053b5bbe07ebe2
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09370569B2

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