ChemicalBook CAS DataBase List 4-(3-Pyridyl)-2-chloropyrimidine

4-(3-Pyridyl)-2-chloropyrimidine synthesis

8synthesis methods

Product Name:4-(3-Pyridyl)-2-chloropyrimidine
CAS Number:483324-01-2
Molecular formula:C9H6ClN3
Molecular Weight:191.62

3934-20-1 Synthesis

3934-20-1
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$9.00/1g

1692-25-7
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$5.00/1g

483324-01-2
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$65.00/10 mg

Yield: 81%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;caesium carbonate in tetrahydrofuran;water at 85; for 12 h;Inert atmosphere;

Steps:

Synthesis of 2-chloro-4-(pyridin-3-yl)pyrimidine (9)
A mixture of 2,4-dichloropyrimidine (7, 2.0 g, 13. 4 mmol), pyridin-3-ylboronic acid (8, 1.65 g 13.4 mmol), CS₂CO₃ (14.2 g, 40. 3 mmol) in THF (45 ml) and H2O (30 ml) was purged under Ar for about 10 minutes. PdCl₂dppf.CH₂Cl₂ (650 mg, 0.81 mmol) was added to the reaction mixture and purged with Ar for another 5 minutes. The reaction mixture was then heated at 85 °C for 12 h. After completion of the reaction, the reaction mixture was cooled to room temperature and passed through a short Celite pad. The filtrate was partioned between EtOAc (60 ml) and H₂O (30 ml). The aq layer was extracted with EtOAc (2 x 30 ml) and the combined organic layer was dried (Na₂SO₄) and concentrated, and the residue was purified on a Biotage Selekt flash purification system (silica gel, 3-5% MeOH/DCM), which afforded 2-chloro-4- (pyrid in-3-yl) pyrimid ine (9) as an off-white solid (2.08 g, 81%). ¹H NMR (400 MHz, DMSO-d₆) δ ppm 9.36 (d, J = 2.4 Hz, 1 H), 8.91 (d, J = 5.2 Hz, 1 H), 8.79 (dd, J = 4.8, 1 .6 Hz, 1 H), 8.56 (dt, J = 8.0, 2.4 Hz, 1 H), 8.27 (d, J = 5.2 Hz, 1 H), 7.63 (dd J = 8.0, 4.8 Hz, 1 H). ESI-MS m/z 192 [M + H]⁺. HPLC: Rt (min): 7.39 (Method 1).