반응 #162639

반응 방정식

3-Oxa-8-azabicyclo[3.2.1]octane, HCl

3-oxa-8-azabicyclo[3.2.1]octane hydrochloride

triethylamine

2,4-dichloro-6-(chloromethyl)pyrimidine

→

8-(2-chloro-6-(chloromethyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane

수율 69.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타to give a yellow solution
2. 2
   농축concentrated
3. 3
   workup.ADDITIONThe crude product was added to a silica gel column
4. 4
   세척eluted with 0-40% ethyl acetate in hexanes

실험 절차

A flask was charged with 2,4-dichloro-6-(chloromethyl)pyrimidine (prepared as reported in Bioorg. Med. Chem., 2002, 10, 525), 2.40 g, 12.15 mmol) in dichloromethane (30 mL) to give a yellow solution. 3-Oxa-8-azabicyclo[3.2.1]octane, HCl (33, 1.818 g, 12.15 mmol) and triethylamine (3.56 ml, 25.5 mmol) in dichloromethane (30 mL) were added slowly over 10 minutes, and the resulting solution was allowed to stir at room temperature for 16 hours, then concentrated. The crude product was added to a silica gel column and eluted with 0-40% ethyl acetate in hexanes to provide 8-(2-chloro-6-(chloromethyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane (2.30 g, 69%) as an off-white solid. HRMS; [M+H]+ Obs'd=274.0510, [M+H]+ Calc'd=274.0508

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