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Sodium Hydroxide → (2S)-4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]-2-methylpiperazine-1-carboaldehyde

HRID 1876601
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1876601
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[N:9]([CH2:30][C:31]([F:34])([F:33])[F:32])[C:10]3[C:15]([N:16]=2)=[C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:13]=[C:12]([C:23]2[CH:24]=[N:25][C:26]([NH2:29])=[N:27][CH:28]=2)[N:11]=3)[CH2:3]1.[CH3:35]N(CCS(O)(=O)=O)C.[OH-:44].[Na+]>O1CCCC1>[NH2:29][C:26]1[N:27]=[CH:28][C:23]([C:12]2[N:11]=[C:10]3[C:15]([N:16]=[C:8]([N:4]4[CH2:5][CH2:6][N:7]([CH:35]=[O:44])[C@@H:2]([CH3:1])[CH2:3]4)[N:9]3[CH2:30][C:31]([F:34])([F:32])[F:33])=[C:14]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[N:13]=2)=[CH:24][N:25]=1
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Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 2370422-(Dimethylamino)ethanesulfonic acidHCID 593335355-{8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine

Produkt 1

HCID 59333623(2S)-4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]-2-methylpiperazine-1-carboaldehydeAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-{8-[(3S)-3-Methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine (107.1 mg, 0.22 mmol) was added to a tetrahydrofuran solution (5.0 ml) of 1H-benzotriazole-1-carboxyaldehyde (36.6 mg, 0.22 mmol) at room temperature and the resulting mixture was stirred for 45 minutes. The reaction mixture was poured into a 2 N aqueous sodium hydroxide solution and the resulting mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1) to give the title compound (100.2 mg, 88%) as a pale yellow solid.

Aufarbeitung

  1. extractionthe resulting mixture was extracted with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationthe mixture was filtrated
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-f1ce0b11d3a0491687ce1d87fb557f30
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309546B2

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