Acetic Acid → HCID 86619269, compound

Participants

Reaction Steps

To a solution of 4-Pyrazol-1-ylmethyl-piperidine hydrochloride salt in 1,2-dichloroethane (5 ml) was added 2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (230 mg) and glacial acetic acid (50 μL). The reaction mixture was stirred at room temperature for 6 hours. Sodium triacetoxyborohydride (224 mg) and triethylamine (113 μL) were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with a 50/50 mixture of saturated sodium bicarbonate solution and brine, dried (MgSO4) and the solvents removed in vacuo to give a crude product. This was purified by flash chromatography to yield 2-Chloro-4-morpholin-4-yl-6-(4-pyrazol-1-ylmethyl-piperidin-1-ylmethyl)-thieno[3,2-d]pyrimidine (154 mg).

Provenance & Evidence