Potassium Carbonate → 9-bromo-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 707472

Reaktionsgleichung

Reaktionsgleichung von HRID 707472
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:21]=[N:20][C:19]2[NH:18][C:17](=[O:22])[N:16]3[N:23]=[CH:24][N:25]=[C:15]3[C:14]=2[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[Br:11][C:12]1[CH:21]=[N:20][C:19]2[N:18]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=3)[C:17](=[O:22])[N:16]3[N:23]=[CH:24][N:25]=[C:15]3[C:14]=2[CH:13]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 1363380329-bromopyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

Produkt 1

HCID 867053859-bromo-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-oneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1-(Chloromethyl)-4-methoxybenzene (3.10 ml, 22.9 mmol) was added to a stirred solution of 9-bromopyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (3.02 g, 11.35 mmol) and potassium carbonate (4.71 g, 34.1 mmol) in 1-methylpyrrolidinone (60 ml) and the mixture was heated at 40° C. for 14 hours. The mixture was filtered, and the resulting solid was washed liberally with dichloromethane. The combined organics were concentrated under vacuum and the residue was triturated with ethyl acetate (40 mL) to afford 3.07 g (70%) of the benzylated product as a brown powder.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe resulting solid was washed liberally with dichloromethane
  3. concentrationThe combined organics were concentrated under vacuum
  4. customthe residue was triturated with ethyl acetate (40 mL)

Quellen und Nachweise

ORD-Eintrag
ord-9f1f0f00d6fc48258b45a252c5d7ad14
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175010B2

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