Chloromethyl methyl sulfide → HCID 58166426, compound

Participants

Reaction Steps

A 250 mL round bottom flask was charged with N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (1.00 g, 5.43 mmol) and DMF (55 mL) to give a white suspension. Solid potassium tert-butoxide (1.07 g, 9.53 mmol) was added, and the resulting pale yellow suspension was allowed to stir under nitrogen at room temperature for 20 min. Chloromethyl methyl sulfide (682 microliters (μL), 8.14 mmol) was then added, and the mixture was heated at 60° C. for 21 h. The crude reaction mixture was concentrated in vacuo at 55° C. to give an off-white residue which was purified by reverse phase column chromatography yielding N′-(5-fluoro-1-methylsulfanylmethyl-2-oxo-1,2-dihydropyrimidin-4-yl)-N,N-dimethylformamidine (36 mg, 25%) as a pale yellow solid: mp 132-136° C.; 1H NMR (400 MHz, CDCl3) δ 8.68 (s, 1H), 8.20 (d, J=3.2 Hz, 1H), 5.40 (s, 2H), 3.19 (s, 3H), 3.07 (s, 3H), 2.20 (s, 3H); IR 2960 (w), 2926 (w), 1640 (s), 1582 (s), 1447 (s), 1382 (m), 1319 (m), 1269 (m), 1108 (m), 1051 (m) cm−1; ESIMS m/z 267 ([M+Na]+).

Provenance & Evidence