Diethyl Ether → HCID 22220860, compound

Participants

Reaction Steps

O-(Mesitylenesulfonyl)hydroxylamine containing ca. 18% water (3.03 g, 2.56 g dry wt., ca. 11.9 mmole) was dissolved in dichloromethane (15 mL) and dried over Na2SO4 and filtered. This was added dropwise to a solution of 4-amino-2,6-dimethylpyrimidine (1 g, 8.12 mmole) in 1:6 methanol-dichloromethane (10.5 mL) in an ice bath with stirring for 2 hr. Ether (20 mL) was added and the mixture was stored at 4 C for 18 hr. The crude aminated product was filtered out and dried (2.65 g). This was dissolved in a minimum amount of methanol, filtered and reduced in volume to ca. 20 mL under reduced pressure. This was diluted with dichloromethane (15 mL) and ether (20 mL) was added, and the mixture was stirred at room temp. for 2 hr. Filtration, washing with 1:1 dichloromethane-ether and drying gave 0.73 g of a fraction, mp 262–264 C, consisting mainly of 1,6(or 4)-diamino-2,4(or 6)-dimethylpyrimidinium mesitylene-2-sulfonate. Storage of the filtrate resulted in deposition of more crystals, which were filtered out and washed with 1:1 dichloromethane-ether to give 1.39 g in two crops of a fraction, mp 194–196 C, consisting mainly of 1,4(or 6)-diamino-2,6(or 4)-dimethylpyrimidinium mesitylene-2-sulfonate. Isomer assignment is tentative.

Provenance & Evidence