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

HRID 421415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421415
[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

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 2370422-(Dimethylamino)ethanesulfonic acidHCID 593335845-{8-[(3R)-3-Methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine

Produkt 1

HCID 59333567(2R)-4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]-2-methylpiperazine-1-carboaldehydeAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-{8-[(3R)-3-Methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine (101.9 mg, 0.21 mmol) was added to a tetrahydrofuran solution (5.0 ml) of 1H-benzotriazole-1-carboxyaldehyde (34.8 mg, 0.21 mmol) at room temperature and the resulting mixture was stirred for 105 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 (96.8 mg, 90%) 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-720db5d43e294efa9d9174933fef6a1e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097622B2

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