4-(2-CHLOROPYRIDO[3,2-D]PYRIMIDIN-4-YL)MORPHOLINE synthesis
- Product Name:4-(2-CHLOROPYRIDO[3,2-D]PYRIMIDIN-4-YL)MORPHOLINE
- CAS Number:53840-89-4
- Molecular formula:C11H11ClN4O
- Molecular Weight:250.68
![2,4-Dichloropyrido[3,2-d]pyrimidine](/CAS/GIF/39551-54-7.gif)
Yield:53840-89-4 90%
Reaction Conditions:
with triethylamine in tetrahydrofuran at 20; for 3 h;Inert atmosphere;Cooling with ice;
Steps:
Procedure for the preparation of 2-chloro-4-morpholin-4-yl-pyrido[3,2-d]pyrimidine) (7)
2,4-Dichloropyrido[3,2-d]pyrimidine (1 eq, 1 gm, 5 mmol) was dissolved in dry THF (100 mL) under inert gas and was kept in an ice bath. A mixture of morpholine (1.05 eq, 456.75 μL, 5.25 mmol) and triethylamine (1.05 eq, 730.37 μL, 5.25 mmol) in dry THF (25 mL) was added dropwise to the previous solution with continuous stirring. The mixture was stirred at room temperature for 3 h. The solvent was removed under reduced pressure. The residue was dissolved in 20 mL chloroform, extracted three times with a saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to afford the title compound without further purification as white solid (1.1 gm, 90%). 1H NMR (CDCl3): δ 3.89 (m, 4H), 4.59 (br s, 4H), 7.61 ( dd, J = 4.2 Hz, J = 8.5 Hz, 1H), 8.12 ( dd, J = 1.7 Hz, J = 8.5 Hz, 1H), 8.95 (dd, J = 1.7 Hz, J = 4.1 Hz, 1H). LCMS, tR = 2.95 min, m/z C11H11ClN4O [M+H]+ = 251.00.
References:
Al-Ashmawy, Aisha A.K.;Ragab, Fatma A.;Elokely, Khaled M.;Anwar, Manal M.;Perez-Leal, Oscar;Rico, Mario C.;Gordon, John;Bichenkov, Eugeney;Mateo, George;Kassem, Emad M.M.;Hegazy, Gehan H.;Abou-Gharbia, Magid;Childers, Wayne [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 14,p. 3117 - 3122] Location in patent:supporting information
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![Pyrido[3,2-d]pyrimidine-2,4(1H,3H)-dione](/CAS/GIF/37538-68-4.gif)
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