Dimethylformamide → HCID 68325557, compound

Participants

Reaction Conditions

Reaction Steps

(R)-tert-Butyl 2-(4-(5-hydroxypyrimidin-2-ylamino)phenyl)morpholine-4-carboxylate (0.24 g) and K2CO3 (124 mg) were combined with DMF (2 ml) to give a brown solution. Ethyl 2-chloro-2,2-difluoroacetate (152 mg) was then added. The reaction mixture was stirred at 80° C. for 1.5 h to afford a dark brown suspension. TLC & HPLC showed the reaction was complete. The reaction mixture was poured into EtOAc and washed sequentially with water and with saturated brine. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel; gradient: 0% to 70% EtOAc in hexanes) to afford (R)-tert-butyl 2-(4-(5-(difluoromethoxy)pyrimidin-2-ylamino)phenyl)morpholine-4-carboxylate (60 mg, 24%) as a yellow oil. MS (ISP): 423.1 ([M+H]+), 367.0 ([M+H—C4H8]+).

Provenance & Evidence