Pyridine → 1,3,6-Trimethyl-2,4(1H,3H)-pyrimidinedione

To a solution of N,N-dimethyl urea (10.0 g, 113.588 mmol) and 4-dimethylamino pyridine (13.873 g, 113.588 mmol) in dry pyridine (30 ml), acetic anhydride (32.20 ml, 340.67 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for overnight. The reaction mixture was quenched into 2 N HCl (250 ml) and extracted with chloroform (2×250 ml). The organic layer was washed with 1 N HCl (100 ml), sodium bicarbonate solution (75 ml), brine (75 ml) and dried (Na2SO4). The solvent was evaporated under reduced pressure to obtain 10.25 g of the product as a yellow solid; 1H NMR (300 MHz, CDCl3) δ 2.24 (s, 3H), 3.33 (s, 3H), 3.40 (s, 3H), 5.62 (s, 1H).

1. customThe reaction mixture was quenched into 2 N HCl (250 ml)
2. extractionextracted with chloroform (2×250 ml)
3. washThe organic layer was washed with 1 N HCl (100 ml), sodium bicarbonate solution (75 ml), brine (75 ml)
4. dry with materialdried (Na2SO4)
5. customThe solvent was evaporated under reduced pressure

ORD record

ord-6c60e729053741f7bb8c05e38e04f695

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987278B2