Acetic Anhydride → 6-chloro-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}pyrido[3,4-d]pyrimidin-4(3H)-one

HRID 2111824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111824
NC1C(C(O)=O)=CC(Cl)=NC=1.C(OC(=O)C)(=O)C.[Cl:19][C:20]1[N:38]=[CH:37][C:23]2[N:24]=[C:25]([CH3:36])[N:26]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)[C:27](=[O:28])[C:22]=2[CH:21]=1.Br.Br[CH2:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:19][C:20]1[N:38]=[CH:37][C:23]2[N:24]=[C:25]([CH3:36])[N:26]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH2:41][CH2:42][CH2:43][N:44]4[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]4)=[CH:33][CH:34]=3)[C:27](=[O:28])[C:22]=2[CH:21]=1

Komponenten

7

Edukt 5

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 201357721-(3-Bromopropyl)piperidine HydrobromideHCID 227367915-Amino-2-chloro-isonicotinic acidHCID 231511466-chloro-2-methyl-3-(4-hydroxyphenyl)pyrido[3,4-d]pyrimidin-4(3H)-one

Produkt 1

HCID 117185676-chloro-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}pyrido[3,4-d]pyrimidin-4(3H)-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Using 5-amino-4-carboxy-2-chloropyridine and acetic anhydride as starting materials, 6-chloro-2-methyl-3-(4-hydroxyphenyl)pyrido[3,4-d]pyrimidin-4(3H)-one synthesized according to Example 1-(1) and -(2) (52 mg, 0.18 mmol), 1-(3-bromopropyl)piperidine hydrobromide (78 mg, 0.27 mmol) and potassium carbonate (100 mg, 0.72 mmol) were mixed in dimethylformamide (1 mL) and stirred at 80° C. for 1 hour. The solvent was distilled off under reduced pressure, distilled water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with distilled water, and dried with anhydrous sodium sulfate. The title compound (45 mg, 60%) was obtained as colorless crystals by purifying with silica gel column chromatography (chloroform/methanol=30/1) and recrystallizing (ethanol).

Aufarbeitung

  1. customsynthesized
  2. distillationThe solvent was distilled off under reduced pressure
  3. distillationdistilled water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with distilled water
  7. dry with materialdried with anhydrous sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-40984d9c46d54c3cad60a5e5f67408f9
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521455B2

Notizen zur Reaktion

Wird geladen…