Ethyl bromoacetate → HCID 56960508, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-((6-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate (250 mg, 0.0004882 mole) in dimethyl formamide (10 ml), sodium hydride (50%, 23.4 mg, 0.0004882 mole) was added at 0° C. and reaction mixture was stirred for 1 hours 30° C. and then ethyl bromoacetate (0.08 ml, 0.000733 mole) was added at 0° C., then reaction mixture was stirred for 3 hours at 30° C. Then reaction mixture was poured into ice cold water and extracted with ethyl acetate. Organic extract was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure to yield crude product. Then crude product was purified through column chromatography using 18% ethyl acetate in hexane as an eluent to yield the product as white solid (160 mg). 1HNMR: δ 1.30 (t, J=7.0 Hz, 3H), 1.48 (s, 9H), 1.76-1.81 (m, 2H), 1.96-2.01 (m, 2H), 2.18 (s, 3H), 3.34-3.41 (m, 2H), 3.71-3.76 (m, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.48 (s, 2H), 5.33-5.35 (m, 1H), 7.55 (d, J=9.6 Hz, 2H), 7.57 (d, J=8.4 Hz, 2H), 7.93 (s, 1H), 8.25 (s, 1H).

Provenance & Evidence