Reaktion #1586212

Reaktionsgleichung

NaBH(OAc)3

NaBH3CN

compound 23

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

azetidine hydrochloride

NaOAc

→

8-Azetidin-1-ylmethyl-2-(1H-indol-4-yl)-4-morpholin-4-yl-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine

Lösungsmittel

brine

EtOAc

MeOH

CH2Cl2

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers were separated
2. 2
   Extraktionextracted with EtOAc (3×10 mL)
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigePurification by flash column chromatography on silica (eluant 2-8% MeOH/CH2Cl2)
6. 6
   Sonstigefurnished U (5.4 mg, 0.012 mmol, 28%) as an off-white solid

Vorschrift

To compound 23 (as per Example S above) (17 mg, 0.04 mmol) in a mixture of dry DMF (2 mL), CH2Cl2 (0.5 mL) and MeOH (0.2 mL) was added azetidine hydrochloride (16 mg, 0.17 mmol) and NaOAc (14 mg, 0.17 mnnol) under Ar(g). After 5 minutes NaBH(OAc)3 (27 m0, 0.13 mmol) and NaBH3CN (5.4 mg, 0.09 mmol) were added and the reaction mixture was stirred for 16 h. EtOAc (45 mL) was added along with 50% saturated brine (5 mL); the layers were separated, extracted with EtOAc (3×10 mL), dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography on silica (eluant 2-8% MeOH/CH2Cl2) furnished U (5.4 mg, 0.012 mmol, 28%) as an off-white solid.

Quelle