Dimethylamine, hydrochloride → HCID 66805417, Verbindung

HRID 1193354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193354
CS([C:5]1[N:6]=[CH:7][C:8]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH2:11][C:9]=2[N:10]=1)(=O)=O.Cl.[CH3:23][NH:24][CH3:25].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[CH3:23][N:24]([CH3:25])[C:5]1[N:6]=[CH:7][C:8]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH2:11][C:9]=2[N:10]=1

Komponenten

6

Edukt 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 22709841tert-Butyl 7,8-dihydro-2-(methylsulfonyl)pyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Produkt 1

HCID 66805417HCID 66805417, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of tert-butyl 2-(methylsulfonyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (2.8 g, 8.95 mmol, 1.0 eq.), dimethylamine HCl (1.09 g, 13.42 mmol, 1.5 eq.) and DIPEA (4.37 ml, 25.56 mmol, 4.0 eq.) in NMP (6.5 ml) was stirred for 1 hour at 130° C. in a microwave. The reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate (2×150 ml). The combined org. phases were washed with sat. NaCl solution (200 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 18% ethyl acetate in hexane). Yield: 78% (1.95 g, 7.01 mmol)

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×150 ml)
  2. washphases were washed with sat. NaCl solution (200 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography (silica gel, 18% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-67eb56693b1d4a289e61b77b65fe6f2f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680159B2

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