ChemicalBook CAS DataBase List 5-AMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE

5-AMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE synthesis

4synthesis methods

Product Name:5-AMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE
CAS Number:49738-24-1
Molecular formula:C6H9N3O2
Molecular Weight:155.15

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5-AMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE

49738-24-1
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Yield:49738-24-1 91%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in ethyl acetate at 20; for 48 h;

Steps:

1,3-Dimethyl-5-aminouracil (4)

A suspension of 220 mg 10% Pd/C (Aldrich) in 140 ml ethyl acetate was stirred at room temperature in hydrogen atmosphere for 30 min, then added solution of 1,3-dimethyl-5-nitrouracil [54] (500 mg, 2.7 mmol) in 50 ml ethyl acetate.The mixture was stirred at r.t. in hydrogen atmosphere for 48h, then filtered and the solvents were removed under reduced pressure to afford a white solid. This solid was recrystallized from ethanol and the thin needle crystals were further dried under vacuum at 40°C until constant weight. Isolated yield 91% (478 mg), m. p. 136-137°C (lit. 136-137°C [55]); ¹HNMR (DMSO-d₆, 500.13 MHz) δH: 3.200 (s, 3H, N(3)CH₃),3.235 (s, 3H, N(1)CH₃), 4.160 (s, 2H, NH₂), 6.849 (s, 1H,CH); ¹³C NMR (DMSO-d₆, 125.76 MHz) δC: 27.66(N(3)CH₃), 35.92 (N(1)CH3), 119.79 (C6), 121.67 (C5),149.40 (C2), 160.33 (C4); ¹⁵N NMR (DMSO-d6, 50.58MHz) δN: 35.3 (NH₂), 112.2 (N1), 151.8 (N₃); Anal. Calcdfor C₆H₉N₃O₂: , 46.45; H, 5.84; N, 27.08. Found: , 46.45;H, 5.88; N, 27.06.

References:

Grabovskiy, Stanislav A.;Antipin, Arcadiy V.;Grabovskaya, Yulia S.;Andriayshina, Nadezhda M.;Akchurina, Oksana V.;Kabal'nova, Natalie N. [Letters in Organic Chemistry,2017,vol. 14,# 1,p. 24 - 32]