Triethylamine → Methyl-2-chloro-4-[3-(methoxymethyl)-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate

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Reaction Steps

3-(Methoxymethyl)-8-azabicyclo[3.2.1]octane (0.106 g, 0.683 mmol) was dissolved in ethanol (2 mL) and dichloromethane (2 mL). Triethylamine (0.166 mL, 1.18 mmol) and methyl 2,4-dichloro-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate (0.200 g, 0.590 mmol) were added and the mixture was stirred at room temperature for 5 hr. It was diluted with dichloromethane (2 mL) and water (2 mL). The layers were separated and the aqueous was extracted with dichloromethane (2×2 mL). The combined organic layers were evaporated to give a yellow oil (281 mg). This was purified by silica chromatography (10 g cartridge; eluent petroleum ether 40-60/ethyl acetate 0 to 20%; all output collected). Fractions corresponding to the main peak were combined and evaporated to give the target compound as a yellow solid (0.177 g). m/z [M+H]+458.0/460.0. Retention time 5.30 min (LCMS method+ve 6 min).

Provenance & Evidence