4-Aminotetrahydropyran → 6-chloro-N-(tetrahydro-2H-pyran-4-yl)-Pyrido[3,2-d]pyrimidin-4-amine

Participants

Reaction Steps

A mixture of 4,6-dichloropyrido[3,2-d]pyrimidine (Intermediate 1, step D) (0.05 g, 0.250 mmol), tetrahydro-2H-pyran-4-amine (0.029 ml, 0.275 mmol), PdCl2(dppf)-CH2Cl2Adduct (2.041 mg, 2.500 μmol) and sodium tert-butoxide (0.048 g, 0.500 mmol) in dioxane (1.250 ml) was refluxed for 3 hours. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and washed with CH2Cl2. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=2:1) to give 6-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrido[3,2-d]pyrimidin-4-amine (0.027 g, 41%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 1.68-1.78 (2H, m), 2.03-2.13 (2H, m), 3.58-3.67 (2H, m), 4.05-4.09 (2H, m), 4.36-4.46 (1H, m), 6.90 (1H, brs), 7.63 (1H, d, J=8.8 Hz), 8.05 (1H, d, J=8.8 Hz), 8.62 (1H, s).

Provenance & Evidence