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

Participants

Reaction Conditions

Reaction Steps

(See, e.g., Azas et al., Farmaco. 58:1263-1270 (2003)). Dimethylsulfate (106 g, 80 ml, 844 mmol) was added dropwise to a solution of 2,4-dihydroxy-6-methylpyrimidine (30 g, 238 mmol) in 280 mL of 4 N NaOH at 40° C. After stirring for 4 h at 40° C., the reaction mixture was neutralized with careful addition of acetic acid and extracted 3 times with 100 mL of ethyl acetate. Combined organics were dried over MgSO4 and concentrated in vacuo to yield a white solid. Recrystallization from ethanol yielded 2 (15.8 g, 43%): mp 113-114° C.; 1H NMR (DMSO-d6): δ 5.58 (s, 1H), 3.26 (s, 3H), 3.09 (s, 3H,), 2.19 (s, 3H,); MS (ES+) (m/z): [M+1]+ calculated for C7H11N2O2, 155.17. found 155.93. This compound matched the analytical data as reported (see, e.g., Azas et al., Farmaco. 58:1263-1270 (2003)).

Provenance & Evidence