Reaktion #1586210

Reaktionsgleichung

NaBH(OAc)3

NaBH3CN

compound 8

[2-(1H-Indol-4-yl)-4-morpholin-4-yl-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidin-8-ylmethyl]-dimethyl-amine

4-fluoropiperidine hydrochloride

NaOAc

→

9

Ausbeute 57.0%

(2-Chloro-4-morpholin-4-yl-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidin-8-ylmethyl)-dimethyl-amine

Ausbeute 57.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe DMF was then removed in vacuo, EtOAc (45 mL)
2. 2
   workup.ADDITIONwas added along with 50% saturated brine (7 mL)
3. 3
   Sonstigethe layers separated
4. 4
   Extraktionextracted with EtOAc (2×15 mL)
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigePurification by flash column chromatography on silica (eluant 1-2% MeOH/CH2Cl2)

Vorschrift

To compound 8 (as per Example H above) (80 mg, 0.25 mmol) in dry DMF (12 mL) was added 4-fluoropiperidine hydrochloride (70 mg, 0.5 mmol) and NaOAc (41 mg, 0.5 mmol) under Ar(g). After 20 minutes NaBH(OAc)3 (106 mg, 0.5 mmol) and NaBH3CN (16 mg, 0.25 mmol) were added and the suspension was stirred for 16 h. The DMF was then removed in vacuo, EtOAc (45 mL) was added along with 50% saturated brine (7 mL), the layers separated, extracted with EtOAc (2×15 mL), dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography on silica (eluant 1-2% MeOH/CH2Cl2) furnished 9 (58 mg, 0.014 mmol, 57%) as a white solid.

Quelle