4-chloro-6-methoxy-2-phenylpyrimidine synthesis
- Product Name:4-chloro-6-methoxy-2-phenylpyrimidine
- CAS Number:4319-72-6
- Molecular formula:C11H9ClN2O
- Molecular Weight:220.65
3740-92-9
124-41-4
4319-72-6
GENERAL STEPS: 4,6-Dichloro-2-phenylpyrimidine (5.0 g, 22.2 mmol) and sodium methanolate (3.6 g, 66.6 mmol) were dissolved in methanol (500 mL) and stirred under ice-bath conditions for 1 hour, followed by heating and refluxing for 7 hours. Upon completion of the reaction, the solvent was removed by evaporation and the resulting white solid was dissolved in dichloromethane (100 mL) and washed with deionized water. The organic phase was separated and concentrated by evaporation to give the target product 4-chloro-6-methoxy-2-phenylpyrimidine (3.98 g, 81% yield) as a white solid. The product was identified by nuclear magnetic resonance hydrogen spectrum (1H NMR, CD3OD): δ 8.39-8.36 (m, 2H), 7.53-7.44 (m, 3H), 6.76 (s, 1H), 4.08 (s, 3H); nuclear magnetic resonance carbon spectrum (13C NMR, CD3OD): δ 172.3, 165.9, 162.2, 137.4, 132.6, 129.5, 129.5, 106.0, 55.0. Mass spectrometry (MS) analysis: calculated value C11H9ClN2O [M+H]+ 221.0, measured value: 221.0.
3740-92-9
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4319-72-6
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Yield:4319-72-6 81%
Reaction Conditions:
with methanol for 8 h;Cooling with ice;Reflux;
Steps:
4 4-Chloro-6-methoxy-2-phenylpyrimidine
4,6-Dichloro-2-phenylpyrimidine (5.0 g, 22.2 mmol) and NaOCH3 (3.6 g, 66.6 mmol) was stirred in methanol (500 mL) on an ice bath for 1 h, then brought to reflux for 7 h.
After evaporation, the white solid was dissolved in DCM (100 mL) and washed with water.
Evaporation of the organic phase yielded 8 (3.98 g, 81%) as a white solid. 1H NMR (CD3OD): δ 8.39-8.36 (m, 2H), 7.53-7.44 (m, 3H), 6.76 (s, 1H), 4.08 (s, 3H).
13C NMR (CD3OD): δ 172.3, 165.9, 162.2, 137.4, 132.6, 129.5, 129.5, 106.0, 55.0. MS calcd for C11H9ClN2O [M+H]+ 221.0, found: 221.0.
References:
Lampa, Anna;Alogheli, Hiba;Ehrenberg, Angelica E.;?kerblom, Eva;Svensson, Richard;Artursson, Per;Danielson, U. Helena;Karlén, Anders;Sandstr?m, Anja [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 23,p. 6595 - 6615]
3740-92-9
243 suppliers
$8.00/10g
124-41-4
725 suppliers
$12.00/25g
4319-72-6
24 suppliers
$45.00/100mg
4319-73-7
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