Uracil, 6-amino-1-methyl-3-propyl- → 2,4(1H,3H)-Pyrimidinedione, 6-amino-1-methyl-5-nitroso-3-propyl-

Participants

Reaction Conditions

Reaction Steps

6-Amino-1-methyl-3-n-propyluracil (13.2 g, 7.3 mmol) was dissolved in 10-15 ml of acetic acid and the solution was warmed on a hot plate to 60-70° C. Then, with stirring, a solution of sodium nitrite (5.3 g, 7.7 mmol) in 100 ml of water was added in 10 ml portions over 10 minutes. A brownish-purple precipitate formed. The reaction mixture was cooled to 10° C. and the precipitate was collected by vacuum filtration, washed with 10 ml of acetone, and air-dried to give 8.3 g (55%) of 6-amino-1-methyl-5-nitroso-3-propyluracil as a purple solid. 1H NMR (DMSO-d6 +D2O) δ 0.90 (t, J=7 Hz, 3 H), 1.62 (sextet, J=7 Hz, 2 H), 3.26 (s, 3 H), 3.87 (t J=7 Hz, 2 H).

Provenance & Evidence