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With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;
<strong>[4983-28-2]2-Chloro-5-hydroxypyrimidine</strong> 34a (0.50 g, 3.8 mmol) was dissolved in N,N-dimethylformamide (5 mL).Benzyl bromide (0.55 mL, 4.6 mmol) and potassium carbonate (0.79 g, 5.7 mmol) were added, and the mixture was reacted at room temperature for 18 hours.The reaction was quenched with water (10 mL).It was extracted with ethyl acetate (20 mL) and the organic phase was washed with saturated sodium chlorideDry over anhydrous sodium sulfate, concentrate by suction filtration, and the residue obtained was purified by silica gel column chromatography[ethyl acetate/petroleum ether (v/v) = 1/10] purified,Get the title compound34b (0.76 g, yield 90percent) as a white solid.
89%
With potassium carbonate; In methanol; at 20℃; for 14h;
Example 9 Synthesis of 2-chloro-5-benzyloxy-pyrimidine Compound 31 Referring to the reaction scheme of , potassium carbonate (11.6 g, 84.3 mmol) was added to 10 g of the alcohol 40 (76.6 mmol) in 500 mL of MeOH, followed by benzyl bromide (10.1 mL, 84.3 mmol). After 14 hrs stirring at r.t., the reaction was stopped by addition of water (300 mL). MeOH was evaporated and the remaining aqueous layer was extracted with CHCl3. The combined CHCl3 layers were washed with brine, dried over magnesium sulfate, and filtered. Removal of the solvent followed by silica gel chromatography using 100:1 CHCl3:MeOH as eluent gave 15 g (89percent) of 2-amino-5-benzyloxy-pyrimidine (31) as a white solid. 1H NMR (CDCl3) delta 8.27 (s, 2H), 7.37-7.30 (m, 5H), 5.09 (s, 2H).
A solution of <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (70percent purity, 7.5g, 40mmol) in DMF (15mL, 190mmol), under argon, was cooled to 0°C. Cesium Carbonate (14. Og, 43mmol) was added, portionwise, and the mixture was stirred for 5min at 0°C then lOmin at r.t.. The mixture was cooled back back down to 0°C and benzyl bromide (5.1mL, 43mmol) was added, portionwise. The reaction was stirred at 0°C for 15min, then allowed to warm to r.t. and stirred for a further 90min. The solvent was removed in vacuo and the residue partitoned between EtOAc and water. The organic phase was separated, washed with water:brine(l : 1), dried (MgS04), and the solvent removed in vacuo. Trituration from a combination of Et20 and IH, and further trituration of the motherliquer after concentration in vacuo, afforded the title compound in two crops: RT = 3.54 min; m/z (ES ) = 221.0 [M+ H]+.
With potassium carbonate; In tetrahydrofuran; at 20℃;Reflux;
Intermediate 8: 2-Chloro-5-benz loxypyrimidine To a stirred mixture of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong> (2.0g, 0.01532mol), K2C03 (4.23g, 0.0307mol) in dry THF (30mL) was added benzyl chloride (2.6mL, 0.023mol) dropwise at room temperature. The mixture was heated at reflux overnight. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure to provide 2-chloro-5-benzyloxypyrimidine (1.3g) which was of sufficient purity to use directly in the synthesis of Intermediate 9.Mass: (ES+) 221 (M+H) +
With potassium carbonate; In tetrahydrofuran;Reflux;
Intermediate 26: 2-Chloro-5-benz loxypyrimidineTo a stirred mixture of 2-chloro 5-hydroxy pyrimidine (2.0g, 0.01532mol), K2C03 (4.23g, 0.0307mol) in dry THF (30mL) was added benzyl chloride (2.6mL, 0.023mol) dropwise at room temperature. The mixture was heated at reflux overnight. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure to provide 2-chloro-5-benzyloxypyrimidine (1.3g) which was of sufficient purity to use directly in the next step.Mass: (ES+) 221 (M+H) +
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