Citric Acid → HCID 66813544, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (108 mg, 2.69 mmol) was added to (S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-hydroxypropanoate (795 mg, 1.97 mmol) (Intermediate AB3) in anhydrous THF (20 mL) at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 10 minutes and then 3-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-4-methylbenzonitrile (Intermediate AM2) (484 mg, 1.79 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was neutralised with 1M citric acid and the reaction mixture diluted with water (10 mL) and EtOAc (30 mL). The organic layer was separated and the aqueous layer re-extracted with EtOAc (2×30 mL). The combined organics were washed with saturated brine (75 mL),dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash silica chromatography, elution gradient 30 to 50% Et2O in isohexane to afford the product (300 mg, 26.3%). m/z (ES+) (M+H)+=636.5; HPLC tR=3.65 min.

Provenance & Evidence