4-Chloro-2,6-dimethoxypyrimidine → HCID 24748349, compound

Participants

Reaction Steps

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(2,6-dimethoxypyrimidin-4-yl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (200 mg, 0.302 mmol) and 6-chloro-2,4-dimethoxypyrimidine following General Procedure A. Flash chromatography (10% EtOAc/hexanes) yielded the title compound as a thick oil (138 mg, 90%): 1H NMR (CDCl3, 400 MHz) 6 7.73 (s, 1H), 7.28-7.24 (m, 2H), 7.18-7.15 (m, 3H), 6.67 (s, 1H), 4.85 (dd, 1H, J=7.3, 5.9 Hz), 4.03 (s, 3H), 4.00 (s, 3H), 2.59 (t, 2H, J=7.6 Hz), 1.96 (m, 2H), 1.62 (m, 2H), 1.36 (m, 4H), 0.90 (s, 9H), 0.10 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 172.3, 166.6, 165.4, 155.2, 149.0, 142.6, 128.3, 128.1, 128.0, 125.5, 95.8, 68.6, 54.8, 53.9, 36.2, 35.8, 31.3, 29.0, 25.6, 25.6, 24.9, 18.1, −5.1, −5.2.

Provenance & Evidence