Stannous chloride dihydrate → 4,6-Dichloro-2-(methylthio)-5-pyrimidineamine

Temperatur

90 °C

To a solution of 4,6-dichloro-2-methylsulfanyl-5-nitro-pyrimidine (1.0 g, 4.2 mmol) in EtOH (20 mL) was added SnCl2.2H2O (3.8 g, 17 mmol). The mixture was heated to 90° C. After 2 h, the reaction mixture was cooled and the solution was concentrated. The residue was treated with saturated (satd.) aqueous (aq.) NaHCO3 until pH 8. The resulting mixture was then extracted with EtOAc (3×100 mL). The combined organic extracts were dried, filtered, and concentrated. The residue was purified by FCC to afford a colorless solid (723 mg, 87%). MS (ESI): mass calcd. for C5H5Cl2N3S, 208.9; m/z found, 210.3 [M+H]+. 1H NMR ((CD3)2SO): 5.89 (s, 2H), 2.45 (s, 3H).

1. temperaturethe reaction mixture was cooled
2. concentrationthe solution was concentrated
3. additionThe residue was treated with saturated (satd.) aqueous (aq.) NaHCO3 until pH 8
4. extractionThe resulting mixture was then extracted with EtOAc (3×100 mL)
5. customThe combined organic extracts were dried
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by FCC

ORD-Eintrag

ord-54919978b75741c2a0c38f1762064981

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09440978B2