5-(2-Methoxyphenoxy)-[2,2'-bipyrimidine]-4,6(1H,5H)-dione synthesis
- Product Name:5-(2-Methoxyphenoxy)-[2,2'-bipyrimidine]-4,6(1H,5H)-dione
- CAS Number:150728-12-4
- Molecular formula:C15H12N4O4
- Molecular Weight:312.28
Yield: 25%
Reaction Conditions:
with ethanol;sodium for 16 h;Heating / reflux;
Steps:
1.3; 2.3
Step 3; 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidine-4,6(1H,5H)-dione: 2-(2-methoxyphenoxy) propanedioic acid diethyl ester (2.82 g, 10 mmol) and a solution of 2-amidinopyrimidine benzenesulfonate (2.8 g, 10 mmol) in ethanol (30 mL) were sequentially added to sodium (0.69 g, 30 mmol) dissolved in absolute ethanol (40 mL). The reaction was heated at reflux for about 16 hours, poured onto ice-water, acidified with 3M hydrochloric acid, and concentrated until a precipitate formed. The precipitate was collected by filtration, washed with water and dried to yield 804 mg of desired product as a yellow solid. (25% yield). 1H NMR (300 MHz, DMSO-d6) δ 3.84 (s, 3H), δ 6.68 (d, J=6.9 Hz, 1H), δ 6.77 (t, J=7.5 Hz, 1H), δ 6.91 (t, J=7.5 Hz, 1H), 7.05 (d, J=6.9 Hz, 1H), 9.05 (d, J=5.1 Hz, 2H), 12.19 (br, 2H); ESI-MS, m/z=313 (M+H+).Step 3 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidine-4,6(1H,5H)-dione: The title compound was made by following the procedure set forth in Example 1, step 3.
References:
AUSPEX PHARMACEUTICALS, INC. US2008/242687, 2008, A1 Location in patent:Page/Page column 32; 34
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