2-Aminopyrimidine → 2-oxo-N-(pyrimidin-2-yl)oxazolidine-3-sulfonamide

Participants

Reaction Steps

In a 200-mL round-bottom flask was charged with DCM (50 mL) and chlorosulfonyl isocyanate (0.913 ml, 10.51 mmol). The flask was cooled in an ice-bath for 20 min, then 2-bromoethanol (0.745 ml, 10.51 mmol) was added dropwise. The mixture was stirred for 2.5 h, then a solution of pyrimidin-2-amine (1.00 g, 10.51 mmol) and triethylamine (4.40 ml, 31.5 mmol) in DCM (30 mL) was added dropwise via an addition funnel over 10 min. When the addition was complete, the cooling bath was removed, and the mixture was stirred for 2 days. The mixture was washed with 2 N aq. HCl, and the aq. layer was extracted with DCM. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The mixture was taken up in a mixture of DCM and EtOAc, then filtered and dried under a stream of nitrogen to give 2-oxo-N-(pyrimidin-2-yl)oxazolidine-3-sulfonamide (0.930 g, 3.81 mmol, 36.2) as a cream-colored solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=12.98 (br. s, 1H), 8.66 (s, 2H), 7.13 (t, J=5.0 Hz, 1H), 4.44-4.18 (m, 4H).

Provenance & Evidence