Nitric Acid → HCID 15485643, compound

Participants

Reaction Conditions

Reaction Steps

To 1.69 g (8.61 mmol) of 1-butyl-3,6-dimethyl-1H-pyrimidine-2,4-dione in 30 mL concentrated H2SO4 at 0° C. was added 1.7 mL fuming HNO3 in drops over 10 min. After stirring at 0° C. for an additional 30 min, the reaction mixture was poured into 300 mL of ice, extracted with 2×150 mL CH2Cl2, and the combined organics were dried over MgSO4, filtered and evaporated to a yellow oil. Flash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (40/1), gave 1.72 g (7.13 mmol, an 83% yield) of the title compound as a light yellow oil. 1H NMR (300 MHz, CDCl3): δ 0.99 (t, J=7.3 Hz, 3H), 1.46 (hex, J=7.3 Hz, 2H), 1.62-1.73 (m, 2H), 2.42 (s, 3H), 3.39 (s, 3H), 3.92 (t, J=7.4 Hz, 2H); IR (KBr, cm-1): 2961s, 2874s, 1722s, 1670s, 1620s, 1363s, 1224m; MS (ES) m/z (relative intensity): 242 (M+ +H, 100). Anal. Calcd for C10H15N3O4 : C, 49.79; H, 6.27, N, 17.42. Found: C, 49.47; H, 6.03; N, 17.37.

Provenance & Evidence