Sodium Hydroxide → 2-(1-bromopropyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 58223

Reaktionsgleichung

Reaktionsgleichung von HRID 58223
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[Br:9][CH:10]([CH2:18][CH3:19])[C:11](=O)[CH2:12][C:13](OC)=[O:14].[OH-].[Na+]>>[Br:9][CH:10]([C:11]1[N:8]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]2[C:13](=[O:14])[CH:12]=1)[CH2:18][CH3:19]

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 157652-Amino-6-methylpyridineHCID 86650061Methyl 4-bromo-3-oxohexanoate

Produkt 1

HCID 668642082-(1-bromopropyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneAusbeute 64,8 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a manually stirred polyphosphoric acid (80 g, 800 mmol) in a 1000 mL beaker at room temperature was added 6-methyl-2-pyridinamine (15 g, 140 mmol), followed by methyl 4-bromo-3-oxohexanoate (37.3 g, 167 mmol). The mixture was heated with stirring at 110° C. for 5 h. After cooling, the dark slurry was transferred into 300 g of ice. The pH of the mixture was adjust to 6-7 with 10% sodium hydroxide. The precipitate was collected by filtration under reduced pressure, washed with water, and air dried to yield the desired product (25.4 g, 64.8%). LCMS calculated for C12H14BrN2O (M+H)+: m/z=281.0. Found: 281.2. 1H NMR (DMSO-d6, 300 MHz) δ 7.66 (1H, d, J=9.0 and 6.9 Hz), 7.39 (1H, d, J=9.0 Hz), 6.90 (1H, d, J=6.9 Hz), 6.33 (1H, s), 4.91 (1H, t, J=7.5 Hz), 2.91 (3H, s), 2.15 (2H, qd, J=7.5 and 7.5 Hz), 0.93 (3H, t, J=7.5 Hz) ppm.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureAfter cooling
  3. filtrationThe precipitate was collected by filtration under reduced pressure
  4. washwashed with water, and air
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-72a6a95511a64b5db4c3ad6114719f9e
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434746B2

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