5-Pyrimidinamine, 2-(methylthio)- (9CI) synthesis

Yield:42382-46-7 84.86%

Reaction Conditions:

with iron⁽⁰⁾;glacial acetic acid in ethanol at 80; for 2 h;Inert atmosphere;

Steps:

163 Example 163. 3-[(3-chloro-2-methoxyphenyl)amino]-2-{2-cyclopropoxypyrido[3,2- d]pyrimidin-8-yl}-1H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-one (compound 771)

To a stirred solution of 2-(methylsulfanyl)-5-nitropyrimidine (5 g, 29.21 mmol, 1.00 equiv) in EtOH (200 mL) was added AcOH (120 mL) and Fe (17 g, 292.11 mmol, 10 equiv) in portions at rt under N₂ atmosphere. The resulting mixture was stirred for 2 h at 80 degrees C under N₂ atmosphere. Desired product could be detected by LCMS. LC-MS: M+H found: 142. The resulting mixture was concentrated under reduced pressure. The resulting mixture was extracted with EA (3 x 100 mL). The combined organic layers were washed with Saturated NaCl (3x100 mL), dried over anhydrous Na₂SO₄. After filtration, the filtrate was concentrated under reduced pressure to afford 2-(methylsulfanyl)pyrimidin-5-amine (3.5 g, 84.86%) as a yellow solid. LC-MS: M+H found: 142.0

References:

WO2022/76831,2022,A2 Location in patent:Page/Page column 711; 712