Reaktion #1865104

Reaktionsgleichung

KHMDS

4-fluoropyridin-2-amine

(S)-tetrahydrofuran-3-ol

KHMDS

→

title compound

(S)-4-((tetrahydrofuran-3-yl)oxy)pyridin-2-amine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting brown solution was stirred for 16 h
2. 2
   workup.STIRRINGthe reaction mixture was stirred at 50° C. for 16 h
3. 3
   SonstigeThe reaction mixture was quenched with sat. aq. NH4Cl
4. 4
   Extraktionextracted with EtOAc (3×)
5. 5
   TrocknenThe combined organic layers were dried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100)

Vorschrift

(S)-tetrahydrofuran-3-ol (707 mg, 8.03 mmol) was treated with KHMDS (1 M in THF, 5.89 ml, 5.89 mmol) and stirred at room temperature for 5 min. Then, the mixture was added to a solution of 4-fluoropyridin-2-amine (300 mg, 2.68 mmol) in THF (15 ml). The resulting brown solution was stirred for 16 h. KHMDS (1 M in THF, 2.68 ml, 2.68 mmol) was added to the reaction and the reaction mixture was stirred at 50° C. for 16 h. The reaction mixture was quenched with sat. aq. NH4Cl and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a pink solid. (UPLC-MS 3) tR 0.30 min; ESI-MS 181.1 [M+H]+.

Quelle