Sodium triacetoxyborohydride → 2-Chloro-9-methyl-6-morpholin-4-yl-8-[2-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)ethyl]-9H-purine

HRID 1922814

Reaktionsgleichung

Reaktionsgleichung von HRID 1922814
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][CH:13]=O)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[CH:21]12[NH:28][CH:25]([CH2:26][CH2:27]1)[CH2:24][O:23][CH2:22]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][CH2:13][N:28]3[CH:21]4[CH2:27][CH2:26][CH:25]3[CH2:24][O:23][CH2:22]4)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 152351793-Oxa-8-azabicyclo(3.2.1)octaneHCID 59605819(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde

Produkt 1

HCID 596059492-Chloro-9-methyl-6-morpholin-4-yl-8-[2-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)ethyl]-9H-purineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of (2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde (117 mg, 0.40 mmol) in DCE (10 mL) was added 3-oxa-8-azabicyclo[3.2.1]octane (54 mg, 0.48 mmol) and powdered 4 Å molecular sieves. The reaction mixture was stirred at room temperature for 2 h, sodium triacetoxyborohydride (168 mg, 0.79 mmol) was added and the resulting mixture stirred for a further 16 h. The reaction mixture was filtered through Celite®, loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography (Si—PCC, 0-10% MeOH in DCM) to give the title compound as a pale yellow oil (80 mg, 51%). LCMS (Method H): RT=2.34 min, [M+H]+ 393.5

Aufarbeitung

  1. stirringthe resulting mixture stirred for a further 16 h
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washwashed with MeOH
  4. washthe desired product eluted with 2 M NH3 in MeOH
  5. customThe resulting residue was purified by column chromatography (Si—PCC, 0-10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-8daab48359ee478b86657294bc20e939
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

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