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CAS No. : | 16632-21-6 | MDL No. : | MFCD00047362 |
Formula : | C5H5N3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LIVYMRJSNFHYEN-UHFFFAOYSA-N |
M.W : | 171.11 | Pubchem ID : | 85523 |
Synonyms : |
5-Nitro-6-methyluracil
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 41.47 |
TPSA : | 111.54 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.74 cm/s |
Log Po/w (iLOGP) : | 0.1 |
Log Po/w (XLOGP3) : | -0.56 |
Log Po/w (WLOGP) : | -0.72 |
Log Po/w (MLOGP) : | -1.77 |
Log Po/w (SILICOS-IT) : | -0.4 |
Consensus Log Po/w : | -0.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.85 |
Solubility : | 24.1 mg/ml ; 0.141 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.31 |
Solubility : | 8.33 mg/ml ; 0.0487 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.23 |
Solubility : | 10.1 mg/ml ; 0.0589 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.06 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
83% | Stage #1: at 0 - 40℃; Stage #2: at 15 - 20℃; for 0.5 h; |
The procedure was adapted from that reported in J. Med. Chem. 1976, 19, 1072. 6-Methylpyrimidine-2,4(lH,3H)-dione (7.Og, 55.56mmol) was added to concentrated sulfuric acid (26 mL) cooled in ice at such a rate that the internal <n="99"/>temperature did not exceed 40°. To this mixture fuming nitric acid (5.2 mL) was added dropwise whilst maintaining the temperature below 15°. The cooling bath was removed and the mixture was stirred at room temperature for 30 min then dumped into 100ml of crushed ice. After stirring for 10 min the solid was collected and washed with cold water then dried in vacuo over phosphorus pentoxide. A yellow-green solid of 6- rnethyl-5-nitropyrimidine-2,4(lH,3H)-dione was obtained (7.92 g, 83percent). |
65.2% | at -2 - 35℃; for 12 h; | The raw material 11 (6.3g) was dissolved in 30ml concentrated sulfuric acid and slowly mixed with low acid (concentrated sulfuric acid / concentrated nitric acid = 10ml / 12ml) at -2 . Finally, the reaction was carried out at 35 for 12h.The reaction solution was poured into ice water and precipitated with a large amount of a pale yellow solid. After filtration under reduced pressure, a pale yellow solid 12 (4 g) was obtained in a yield of 65.2percent. |
2.7 g | at 50℃; for 10 h; Inert atmosphere | To a stirred mixture of 96percent H2S04(15 mL) and of 70percent HN03(15 mL) was added 6- methyl pyrimidine-2,4-(lH,3H)-dione (2.5 g,19.8 mmol). The solution was kept at 50 °C for lOh. The mixture was cooled to room temperature and poured into a large volume of ice water. The solid was collected and dried in vacuo. Recrystallization with MeOH gave the final compound (2.7g,16.2 mmol) as yellows solid.1H NMR (200 MHz,DMSO) δ 2.31 (s,3H), 11.82 (s,1H), 11.85 (s,1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate In N,N-dimethyl-formamide at 120℃; for 8 h; | The raw material 12 (1 eq) was dissolved in 17.54 ml of phosphorus oxychloride, and 2.92 ml of N, N-dimethylaniline (1 eq) was slowly added dropwise at room temperature, and 8.04 ul of DMF (0.00445 eq) 120 under reflux reaction 8h, after the completion of the reaction of raw materials, vacuum distillation of phosphorus oxychloride, adding ice water, adding ethyl acetate extraction, combined organic layer, washed with saturated brine, dried over anhydrous sodium sulfate, spin dry Solvent to give a yellowish brown oil which was dryly chromatographed and finally purified to give a yellow solid 13 (1 g) in 65percent yield. |
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