Dimethylformamide → 3-[2-(5-Chlorothieno[2.3-d]pyrimidin-4-ylamino)ethyl]phenol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Into a 250-mL, 3-necked, round-bottom flask, equipped with a mechanical stirrer, condenser, dropping funnel, and thermocouple temp monitor, under an atmosphere of nitrogen was added N,N-dimethylformamide (75 mL) , 4,5-dichlorothieno[2,3-d]pyrimidine (7.47 g, 36 mmol), 3-hydroxyphenethylamine hydrochloride (5.0 g, 28.8 mmol), and triethylamine (10.7 mmol). After exothermic mixing of the reagents raised the temperature of the reaction mixture to 33° C., the mixture was allowed to stir overnight while returning to 25° C. Then the mixture was poured into water and extracted with warm (60° C.) ethyl acetate (5×70 mL). The combined organic phases were washed with water (2×70 mL), brine (70 mL), dried (MgSO4), filtered through silica gel/Celite plug, and most of the solvent removed in vacuo to give a yellow oil. The oil was dissolved in ethyl acetate (100 mL), heated to reflux, and allowed to cool to 25° C. A yellow crystalline solid formed, and was removed via suction filtration; the product was air dried on the funnel for 3 h, to give 6.34 g, 20.8 mmol, 72 percent yield, 164-165° C.

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