Structure of 1627-27-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1627-27-6 |
Formula : | C6H8N2O2 |
M.W : | 140.14 |
SMILES Code : | O=C1NC(C=C(C)N1C)=O |
MDL No. : | MFCD00456725 |
InChI Key : | OCUWGDBSGJMUNG-UHFFFAOYSA-N |
Pubchem ID : | 10606818 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.1% | With sulfuric acid; potassium nitrate; at 0 - 20℃; for 20h;Inert atmosphere; | Step 2: 1 ,6-dimethyl-5-nitro rimidine-2,4(l H,3H)-dioneTo a solution of l,6-dimethylpyrimidine-2,4(lH,3H)-dione (5 g, 0.035 mol) in S04 (20 mL) at 0C was added dropwise a solution of N03 (4.69 g, 0.046 mol) in H2S04 (10 mL). The reaction was stirred 0C for 2 h, warmed to RT, stirred for 18 h, poured into ice then extracted with EA (5x50 mL). The combined organic layers were dried over Na S04, and concentrated to give 1 ,6- dimethyl-5-nitropyrimidine-2,4(lH,3H)-dione (4.3 g, 68.1% yield) as a yellow solid. NMR (DMSO-<) δ: 12.09 (s, 1H), 3.32 (s, 3H), 2.36 (s, 3H) LCMS: MH+ 186 and TR = 0.610 min. Used without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | at 100℃; for 18h;Inert atmosphere; | Step 1 : 1 ,6-dimethylpyrimidine-2,4(l H,3H)-dioneA solution of 1-methylurea (30 g, 0.356 mol) in 4-methyleneoxetan-2-one (26.4 g, 0.356 mol) was heated at 100C for 18 h, cooled to RT then diluted with MeOH (50 mL). The reaction was filtered and the filtered solid was washed with MeOH (20 mL) and dried to give 1,6- dimethylpyrimidine-2,4(lH,3H)-dione (9 g, 8% yield) as a white solid. ]H NMR (CDClj) 6: 8.33 (s, 1H), 5.58 (s, 1H), 3.38 (s, 3H), 2.26 (s, 3H). LCMS: MH+ 141 and TR = 0.368 min. Used without further purification. |
14% | In acetic acid; at 120℃; for 12h; | 4-Methyleneaxetan-2-one (8.0 g, 95 mmol) and N-methylurea (5.0 g, 68 mmol) were dissolved in acetic acid (50 ml), followed by stirring at 120 C. for 12 hours. The solvent was removed under reduced pressure. To the obtained residue, ethyl acetate (50 ml) was added, followed by stirring for 30 minutes. After the precipitated solid was filtered, purification was conducted by reversed-phase HPLC (H2O containing 0.1% FTA/CH3CN system) to obtain the title compound (1.3 g, 14%). [0618] 1H NMR (400 MHz, CD3OD): δ 5.59 (s, 1H), 3.39 (s, 3H), 2.32 (s, 3H) |