4,6-dichloro-2-(propylthio)pyriMidine synthesis

Yield: 2.3 g

Reaction Conditions:

with trichlorophosphate for 18 h;Reflux;

Steps:

4,6-dichloro-2-(propylthio)pyrimidine (7)
Asolution of 6 (3.3 g, 17.7 mmol) in POCl₃(25 ml) was refluxed for 18 h. The reaction mixture was then poured into crushed ice and extracted with EtOAc (3 x 200 ml). The combined organic layers were dried over MgSO₄, filtered and the solvent was removed under vacuum. The crude product was purified by column chromatography (SiO₂,heptane: Et₂O, 95:5) to afford 7(2.3 g, 58%) as an oily liquid. HRMS(EI) calcd for C₇H₈Cl₂N₂S: m/z221,9785 [M]⁺, found: m/z 221.9785; ¹HNMR (300 MHz, CDCl₃, ppm) d: 7.02 (s, 1H), 3.13(t, 2H, J = 7.3 Hz), 1.77 (sextet, 2H, J = 7.3 Hz), 1.05 (t, 3H, J = 7.3 Hz); ¹³CNMR (75 MHz, CDCl₃, ppm) d: 174.4, 161.3, 115.7,33.3, 22.1, 13.4; IR (ATR) ν_max (cm^-1) 3108, 2964, 2932, 2873

References:

Merckx, Tamara;Verwilst, Peter;Dehaen, Wim [Tetrahedron Letters,2013,vol. 54,# 32,p. 4237 - 4240] Location in patent:supporting information