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Tetrahydrofuran → 4-{2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-8-yl}piperazine-1-carboaldehyde

HRID 1876627
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Reaktionsgleichung

Reaktionsgleichung von HRID 1876627
[O:1]1CCC[CH2:2]1.[CH2:6]([N:10]1[C:18]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:17][C:16]2[C:11]1=[N:12][C:13]([C:32]1[CH:33]=[N:34][C:35]([NH2:38])=[N:36][CH:37]=1)=[N:14][C:15]=2[N:25]1[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]1[CH3:31])[CH:7]([CH3:9])[CH3:8].N1(C=O)C2C=CC=CC=2N=N1.[OH-].[Na+]>CCOCC.C(Cl)(Cl)Cl>[NH2:38][C:35]1[N:36]=[CH:37][C:32]([C:13]2[N:12]=[C:11]3[C:16]([N:17]=[C:18]([N:19]4[CH2:24][CH2:23][N:22]([CH:2]=[O:1])[CH2:21][CH2:20]4)[N:10]3[CH2:6][CH:7]([CH3:9])[CH3:8])=[C:15]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]3[CH3:31])[N:14]=2)=[CH:33][N:34]=1
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Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 593335555-{9-Isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine

Produkt 1

HCID 593336504-{2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-8-yl}piperazine-1-carboaldehyde
Ausbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A tetrahydrofuran (3 ml) solution of 5-{9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine (103 mg, 0.23 mmol) and 1H-benzotriazole-1-carboaldehyde (37 mg, 0.25 mmol) was stirred at room temperature for 16 hours. Chloroform and 2 N aqueous sodium hydroxide solution were added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (methylene chloride:methanol=95:5) to give a solid. Ether was added to the resulting solid and the solid was collected by filtration and dried to give the title compound (86 mg, 79%) as a powder.

Aufarbeitung

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationafter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography (methylene chloride:methanol=95:5)
  6. customto give a solid
  7. filtrationthe solid was collected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2eb6ef3adb4c46cd9d72e84b31213320
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309546B2

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