N-methyl-2-pyrrolidone → 5-{8-[(3S)-3-Ethylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine

HRID 1876572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876572
C(N(C(C)C)CC)(C)C.CN1CCCC1=O.[CH2:17]([C@H:19]1[CH2:24][NH:23][CH2:22][CH2:21][NH:20]1)[CH3:18].[NH2:25][C:26]1[N:31]=[CH:30][C:29]([C:32]2[N:40]=[C:39]3[C:35]([N:36]=[C:37](Cl)[N:38]3[CH2:41][C:42]([F:45])([F:44])[F:43])=[C:34]([N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)[N:33]=2)=[CH:28][N:27]=1>O>[CH2:17]([C@@H:19]1[NH:20][CH2:21][CH2:22][N:23]([C:37]2[N:38]([CH2:41][C:42]([F:43])([F:45])[F:44])[C:39]3[C:35]([N:36]=2)=[C:34]([N:47]2[CH2:48][CH2:49][O:50][CH2:51][CH2:52]2)[N:33]=[C:32]([C:29]2[CH:28]=[N:27][C:26]([NH2:25])=[N:31][CH:30]=2)[N:40]=3)[CH2:24]1)[CH3:18]

Komponenten

6

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 11240458(2S)-2-EthylpiperazineHCID 593335342-(2-aminopyrimidin-5-yl)-8-chloro-6-(morpholin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purine

Produkt 1

HCID 593335585-{8-[(3S)-3-Ethylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amineAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Diisopropylethylamine (1.48 ml, 8.49 mmol) was added to an N-methyl-2-pyrrolidone suspension (4 ml) of 2-(S)-ethylpiperazine 2 hydrochloride (529 mg, 2.83 mmol) and 2-(2-aminopyrimidin-5-yl)-8-chloro-6-(morpholin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purine (391 mg, 0.94 mmol) and the resulting mixture was stirred at 100° C. for 4 days. Water was added to the reaction mixture and the resulting mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography (chloroform:methanol=97:3 to 90:10) to give the title compound (379 mg) as a pale yellow solid.

Aufarbeitung

  1. extractionthe resulting mixture was extracted twice with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationthe mixture was filtrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel chromatography (chloroform:methanol=97:3 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-f92a75927ad84e5cacc667cfc3288593
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309546B2

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