2-Chloro-5-nitropyrimidine → HCID 53260086, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of 3-(1-adamantyl)-4-benzyloxyphenylboronic acid (1) (833 g, 2.3 mmol) and 2-chloro-5-nitropyrimidine (2) (320 mg, 2.00 mmol) in degassed toluene (15 mL) was added tetrakis(triphenylphosphine)palladium (347 mg, 0.300 mmol), NaHCO3 (336 mg, 4.00 mmol) and degassed H2O (3 mL). The mixture was heated at reflux (90° C. oil-bath) for 24 h, cooled to room temperature and extracted with EtOAc (180 mL). The extract was washed (H2O and brine) and dried. After solvent removal at reduced pressure, the residue was chromatographed (3% EtOAc/hexane) to give 165 mg (19%) of 2-[3-(1-adamantyl)-4-benzyloxyphenyl]-5-nitropyrimidine as a yellow solid, mp 206° C. (dec). IR 2902, 1405, 1179 cm−1; 1H NMR (CDCl3) δ 1.76 (bs, 6H, AdCH2), 2.09 (bs, 311, AdCH), 2.22 (m, 6H, AdCH2), 5.24 (s, 2H, C6H5CH2), 7.07 (d, J=8.7 Hz, 1H, 5′-ArH), 7.34-7.53 (m, 5H, C6H5), 8.40 (dd, J=8.7 Hz, 2.4 Hz, 1H, 6′-ArH), 8.51 (d, J=2.4 Hz, 1H, 2′-ArH), 9.46 ppm (s, 2H, 4-ArH, 6-ArH). HRMS calcd C27H27N3O3 [M+H]+ 442.2125. found 442.2137.

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