반응 #70591

반응 방정식

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

용매

DMF

반응 조건

후처리

1. 1
   기타prepared
2. 2
   온도The mixture was cooled to room temperature
3. 3
   여과filtered through Celite
4. 4
   세척washing with hot ethyl acetate
5. 5
   기타Solvent was removed under reduced pressure
6. 6
   기타the 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

실험 절차

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.

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