Sodium triacetoxyborohydride → 2-(1-((2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol

HRID 1692874

Reaktionsgleichung

Reaktionsgleichung von HRID 1692874
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:17]=O)[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1.[NH:25]1[CH2:30][CH2:29][CH:28]([C:31]([OH:34])([CH3:33])[CH3:32])[CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:17][N:25]3[CH2:30][CH2:29][CH:28]([C:31]([OH:34])([CH3:33])[CH3:32])[CH2:27][CH2:26]3)[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1

Komponenten

6

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 52003212-(4-Piperidyl)-2-propanolHCID 596034642-chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine-8-carbaldehyde

Produkt 1

HCID 596035392-(1-((2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-olAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-8-carbaldehyde (245 mg, 0.696 mmol), 2-(4-piperidyl)-2-propanol (110 mg, 0.77 mmol) and sodium triacetoxyborohydride (162 mg, 0.77 mmol) in 1,2-dichloroethane (10 mL) was stirred at room temperature for 30 minutes. The reaction mixture was then diluted with saturated aqueous sodium bicarbonate. The aqueous layer was then extracted with DCM. The combined organic extracts were then washed with water, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (0-100% gradient EtOAc-heptane) to give the title compound (328 mg, 98%). LCMS: M+H+=480.2.

Aufarbeitung

  1. extractionThe aqueous layer was then extracted with DCM
  2. washThe combined organic extracts were then washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0-100% gradient EtOAc-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-2e57d51323a34bf2ab721a3ded651eae
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158625B2

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