N-Iodosuccinimide → 2-(1-bromopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1429771

Reaktionsgleichung

Reaktionsgleichung von HRID 1429771
[Br:1][CH:2]([C:5]1[N:6]=[C:7]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:8]2[C:9](=[O:11])[CH:10]=1)[CH2:3][CH3:4].[I:17]N1C(=O)CCC1=O>C(#N)C>[Br:1][CH:2]([C:5]1[N:6]=[C:7]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:8]2[C:9](=[O:11])[C:10]=1[I:17])[CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 668642082-(1-bromopropyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Produkt 1

HCID 668641442-(1-bromopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-(1-bromopropyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (3.46 g, 12.3 mmol) and N-iodosuccinimide (4.15 g, 18.4 mmol) in acetonitrile (100 mL) was stirred at 80° C., under nitrogen, overnight. After removal of acetonitrile in vacuum, the resulting solid was dissolved in methylene chloride, washed with water, saturated Na2S2O3, saturated sodium bicarbonate, and brine; and then the organic layers dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure to provide the desired product (4.53 g, 90.4%). LCMS calculated for C12H13BrIN2O (M+H)+: m/z=406.9. Found: 407.1.

Aufarbeitung

  1. customAfter removal of acetonitrile in vacuum
  2. dissolutionthe resulting solid was dissolved in methylene chloride
  3. washwashed with water, saturated Na2S2O3, saturated sodium bicarbonate, and brine
  4. dry with materialand then the organic layers dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-edfb703bdc5042b88ce80d3c96c25ad6
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940752B2

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