2-Chloro-5-(phenylmethoxy)-pyrimidine synthesis
- Product Name:2-Chloro-5-(phenylmethoxy)-pyrimidine
- CAS Number:138274-14-3
- Molecular formula:C11H9ClN2O
- Molecular Weight:220.65
100-39-0
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138274-14-3
Example 9: Synthesis of 2-chloro-5-(phenylmethoxy)pyrimidine (compound 31) Under the guidance of the reference reaction scheme, potassium carbonate (11.6 g, 84.3 mmol) was added to a 500 mL methanol solution containing 10 g of 2-chloro-5-hydroxypyrimidine (76.6 mmol), followed by benzyl bromide (10.1 mL, 84.3 mmol). The reaction mixture was stirred at room temperature for 14 hours. Upon completion of the reaction, water (300 mL) was added to terminate the reaction. Methanol was removed by evaporation and the remaining aqueous layer was extracted with chloroform. The combined chloroform layers were washed with brine, dried with anhydrous magnesium sulfate and filtered. After removal of the solvent, the product was purified by silica gel column chromatography using 100:1 chloroform:methanol as eluent to afford 15 g (89% yield) of 2-chloro-5-(phenylmethoxy)pyrimidine (31) as a white solid. 1H NMR (CDCl3) δ 8.27 (s, 2H), 7.37-7.30 (m, 5H), 5.09 (s, 2H).
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Yield: 92%
Reaction Conditions:
with caesium carbonate in N,N-dimethyl-formamide at 15; for 8 h;Inert atmosphere;
Steps:
1 Step 1: 5-(Benzyloxy)-2-chloropyrimidine
To a mixture of 2-chloropyrimidin-5-ol (45 g, 345 mmol) in DMF (1 L) was added Cs2CO3(337 g, 1034 mmol) and (bromomethyl)benzene (49.1 mL, 414 mmol). The mixture was stirred at 15 °C for 8 h under N2 atmosphere. Then the mixture was concentrated and saturated aqueous NaHCO3solution (150 mL) was added. The aqueous layer was extracted with EtOAc (500 mL x 2), and the combined extracts were washed with brine (150 mL x 2), dried over Na2SO4, filtered and concentrated to yield a yellow oil of 5-(benzyloxy)-2-chloropyrimidine (78 g, 318 mmol, 92.0% yield):1H NMR (400 MHz, CD3OD) δ ppm 8.45 (s, 2H), 7.52-7.29 (m, 5H), 5.23 (s, 2H); ES-LCMS m/z 221.2, 223.1 [M+H]+.
References:
BP ASSET V, INC. WO2021/97009, 2021, A1 Location in patent:Paragraph 00172
100-44-7
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4983-28-2
273 suppliers
$6.00/250mg
138274-14-3
123 suppliers
$15.00/100mg