2-Pyridinamine, 5-bromo-6-methyl- → HCID 178469685, Verbindung

HRID 1280455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280455
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13](=[C:17]([C:21]([O-])=O)[C:18]([O-])=[O:19])[O:14]CC)[CH3:11]>>[Br:9][C:5]1[CH:4]=[C:3]2[C:2](=[N:7][C:6]=1[CH3:8])[N:1]=[CH:21][C:17]([C:13]([O:12][CH2:10][CH3:11])=[O:14])=[C:18]2[OH:19]

Komponenten

3

Edukt 2

HCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 23435867Diethoxymethylenemalonate

Produkt 1

HCID 178469685HCID 178469685, VerbindungAusbeute 35 %

Reaktionsbedingungen

Temperatur
250 °C

Versuchsvorschrift

A solution of 6-amino-3-bromo-2-methylpyridine (1.89 g, 10 mmol) and diethoxymethylenemalonate (2.16 g, 10 mmol) is heated at 110° C. for 30 min. The reaction is cooled and the residue is recrystallized from EtOH. To the resulting solid is dissolved in 45 mL of Ph2O. The mixture is heated to 250° C. for 3 h. The solution is then cooled to room temperature and the resulting precipitate is collected and dried. The crude product is chromatographed on silica (Biotage flash 40M, 2% MeOH/CH2Cl2 eluent). Fractions homogeneous by TLC are collected and concentrated to yield 1.075 g (35%) of the desired product as a yellow solid. Physical data are as follows: m.p. 270° C. (dec.); 1H NMR (DMSO-d6) δ 12.73, 8.49, 8.47, 4.21, 2.67, 1.27.

Aufarbeitung

  1. temperatureThe reaction is cooled
  2. customthe residue is recrystallized from EtOH
  3. dissolutionTo the resulting solid is dissolved in 45 mL of Ph2O
  4. temperatureThe solution is then cooled to room temperature
  5. customthe resulting precipitate is collected
  6. customdried
  7. customThe crude product is chromatographed on silica (Biotage flash 40M, 2% MeOH/CH2Cl2 eluent)
  8. customFractions homogeneous by TLC are collected
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ce3f2991dff14eb59e8c8ae7f68f8be7
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451811B2

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