Chloromethyl methyl sulfide → HCID 58166426, compound

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]+).

1. customto give a white suspension
2. temperaturethe mixture was heated at 60° C. for 21 h
3. customThe crude reaction mixture
4. concentrationwas concentrated in vacuo at 55° C.
5. customto give an off-white residue which
6. customwas purified by reverse phase column chromatography

ORD record

ord-509664b5606c448f8d071770a91689e3

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916579B2