Sodium triacetoxyborohydride → 1-[1-(2-Chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-ylmethyl)azetidin-3-yl]piperidin-4-ol

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Reaction Steps

A mixture of 2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carbaldehyde (136 mg, 0.48 mmol), 1-azetidin-3-ylpiperidin-4-ol (90 mg, 0.58 mmol) and 4 Å powdered molecular sieves (260 mg) in DCE (15 mL) was stirred for 5 h before the addition of sodium triacetoxyborohydride (202 mg, 0.96 mmol). The resulting mixture was stirred for 18 h then filtered through Celite® and the filtrate loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH/DCM. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound as a pale yellow oil (153 mg, 75%). LCMS (method H): RT 1.88 min [M+H]+ 424.3

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