반응 #1886018

반응 방정식

4-fluoropyridinium chloride

Sodium hydride

DMF

rac-trans 2-{2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol

→

titled compound

rac-trans-5-chloro-2-(4-{2-[2-(pyridin-4-yloxy)ethyl]cyclopropyl}piperidin-1-yl)pyrimidine

용매

ethyl acetate

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred at room temperature for 10 min
3. 3
   온도The mixture was heated to 50° C. for 1.5 hours
4. 4
   온도cooled to room temperature
5. 5
   기타quenched with saturated aq
6. 6
   건조NH4Cl (5 mL), dried over MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타The crude residue was purified by silica gel chromatography (30% ethyl acetate/hexane)

실험 절차

Sodium hydride (100%, 20 mg, 0.85 mmol) was weighed into a vial, DMF (anhydrous, 2.1 mL) was added, followed by addition of rac-trans 2-{2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol (60 mg, 0.21 mmol) and the mixture stirred at room temperature for 5 min. The 4-fluoropyridinium chloride was then added and stirred at room temperature for 10 min. The mixture was heated to 50° C. for 1.5 hours, cooled to room temperature, and diluted with ethyl acetate (5 mL), quenched with saturated aq.NH4Cl (5 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified by silica gel chromatography (30% ethyl acetate/hexane) to yield the titled compound as a white solid. LC-MS (M+1): 359.54. Compounds Reported in Table 3 are Prepared by a General Procedure Analogous to that Described in Example 6, Steps 1 and 2, Described Above

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