Methyl iodide → 4-Methyl-2-(methylsulfanyl)pyrimidine

Participants

Reaction Steps

Based on a reported procedure (Ishizumi, K.; Kojima, A.; Antoku, F. Chem Pharm Bull 1991, 39, 2288). Sodium hydroxide (92.5 g, 2.31 mol) was added to a suspension of 2-mercapto-4-methylpyrimidine hydrochloride (150 g, 0.93 mol) in water (1.5 L). Methyl iodide (78.9 ml, 1.39 mol) was rapidly added to the clear solution (solution temp.<20° C.). After overnight stirring, diethyl ether (400 mL), the organic layer was separated and the aqueous layer was extracted with diethyl ether (4×200 ml) all organic layers were combined, washed with 5% aq. NaOH solution (100 ml), brine (200 ml, 2 times), and dried (MgSO4), concentrated in vacuo to afford 119.3 g of crude material (95% pure by NMR) which was used in the next step without purification. 1H NMR (CDCl3, 300 MHz) δ, ppm: 2.46 (s, 3H), 2.56 (s, 3H), 6.82 (d, J=5 Hz, 1H,), 8.37 (d, J=5 Hz 1H).

Provenance & Evidence