反応 #70591

反応方程式

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

cesium carbonate

5-bromo-2-phenylpyrimidine

tert-butyl-4-thiazolecarboxylate

→

title compound

tert-butyl 2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxylate

溶媒

DMF

反応条件

後処理

1. 1
   その他prepared
2. 2
   温度The mixture was cooled to room temperature
3. 3
   ろ過filtered through Celite
4. 4
   洗浄washing with hot ethyl acetate
5. 5
   その他Solvent was removed under reduced pressure
6. 6
   その他the residue purified by silica gel flash chromatography (9:1 to 3:2 v/v hexane-ethyl acetate gradient) through a 40-g Silicycle® flash silica cartridge

実験手順

In a sealed tube, cesium carbonate (1.95 g, 6.00 mmol), tert-butyl-4-thiazolecarboxylate (556 mg, 3.00 mmol; prepared according to the procedure described in Organic Letters, 2008, 10(13), 2909), palladium(II) acetate (47 mg, 0.21 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (240 mg, 0.42 mmol) were combined with 5-bromo-2-phenylpyrimidine (705 mg, 3.00 mmol) in dry DMF (11 mL) and the mixture heated at 110° C. for 18 hours with stirring. The mixture was cooled to room temperature and filtered through Celite washing with hot ethyl acetate. Solvent was removed under reduced pressure and the residue purified by silica gel flash chromatography (9:1 to 3:2 v/v hexane-ethyl acetate gradient) through a 40-g Silicycle® flash silica cartridge. The title compound was obtained as a white solid (646 mg, 63% yield); Rf 0.75 with 1:1 v/v hexane-ethyl acetate; 1H-NMR (300 MHz; CDCl3) δ 9.37 (s, 2H), 8.52 (dd, 2H), 8.15 (s, 1H), 7.54 (m, 3H), 1.64 (s, 9H); MS (ESI+) m/z 340 (M+1); H-PGDS FPBA IC50: 5.9 μM.

出典