Реакция #162639

Уравнение реакции

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

Выход 69.0%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

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

Методика

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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