Sodium Bicarbonate → 4'-Hydroxy-6-trifluoromethyl-3',4',5',6'-tetrahydro-2'h-[2,4']bipyridinyl-1'-carboxylic acid(7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

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Reaction Steps

A mixture of 6-trifluoromethyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol (320 mg, 1.30 mmol) in acetonitrile (15 mL) was treated with (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-carbamic acid phenyl ester (360 mg, 1.18 mmol). The mixture was stirred at reflux for 2 h. At this time, the reaction was poured into a saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with methylene chloride. The organics were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 98/2 methylene chloride/methanol) afforded 4′-hydroxy-6-trifluoromethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (94 mg, 17%) as a white solid; LRMS for C18H17F3N6O3S (M+H)+ at m/z=454. The NMR spectrum obtained on the sample is compatible with its structure.

Provenance & Evidence