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CAS No. : | 150728-12-4 | MDL No. : | MFCD09879703 |
Formula : | C15H12N4O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZJMPECSQUMNGPA-UHFFFAOYSA-N |
M.W : | 312.28 | Pubchem ID : | 11109730 |
Synonyms : |
|
Num. heavy atoms : | 23 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.13 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 85.94 |
TPSA : | 102.77 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) : | -7.4 cm/s |
Log Po/w (iLOGP) : | 1.53 |
Log Po/w (XLOGP3) : | 1.13 |
Log Po/w (WLOGP) : | -0.43 |
Log Po/w (MLOGP) : | 0.32 |
Log Po/w (SILICOS-IT) : | 1.76 |
Consensus Log Po/w : | 0.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.61 |
Solubility : | 0.766 mg/ml ; 0.00245 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.88 |
Solubility : | 0.41 mg/ml ; 0.00131 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.76 |
Solubility : | 0.0054 mg/ml ; 0.0000173 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.54 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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% | With sodium ethanolate In methanol at 5℃; Large scale | 2-Cyanopyrimidine (14, 25 kg, 237.87 mol) was added to a solution of sodium ethoxide(1.62 kg, 23.78 mol) inmethanol (400 L) at 0–5C. The reactionmixture was stirred for 6 h at0–5C, and the reaction temperature was raised to 25–30C. Ammonium chloride (13.36 kg,249.76 mol) was added and the mixture was stirred for 4 h at 25–30C to yield 2 followed bythe addition of dimethyl 2-(2-methoxyphenoxy)malonate (1, 79.22 kg, 311.6 mol) at 0–5C.Sodium ethoxide (55 kg, 808.75 mol) was added in portion wise for 1 h at 0–5C, the reactionmixture was heated and stirred for 5 h at 35–40C. After completion of the reaction, de-mineralizedwater (1100 L) was added at 20–30C, and the pH was adjusted to 0.5–0.7 with 1 Naqueous hydrochloric acid at 20–30C for 1 h and stirred for 1 h. The precipitated product wascollected, washed with de-mineralized water (50 L) and dried at 75–80C to give compound 3as a light brown solid (61.36 kg, 83percent yield and purity of 99.98percent) mp. 262–264C. DSC:279.11C and MSM/z (ESI): 311.2 [(MCH)]; 1H NMR (DMSO, 300 MHz): d 3.83 (s, 3H),6.66–6.69 (dd, 1H), 6.77–6.82 (dd, 1H), 6.94–6.96 (dd, 1H), 7.03–7.06 (dd, 1H), 7.73 (dd, 1H),9.03–9.05 (d, 2H), 12.39 (brs, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium t-butanolate In ethanol for 1 h; Inert atmosphere | The 2 - (2 - methoxy phenoxy) malonamide (II) (35.0 g, 156.1 mmol) dissolved in ethanol (600 ml) in, are tertiary butanol sodium (30.0 g, 312.2 mmol) and 2 - pyrimidine formic acid ethyl ester (III) (23.8 g, 156.1 mmol), stirred under the protection of nitrogen reflux 1 h, TLC detection reaction is completed. Recovering the ethanol, the residue with water (200 ml) mixed beating, filtering, a little water to wash the filter cake, drying, to obtain compound 5 - (2 - methoxyphenoxy) - 1H - [2, 2'] - bipyridyl - 4, 6 - dione (IV) 40.5 g, yield is 83percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | for 16 h; Heating / reflux | Step 3; 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidine-4,6(1H,5H)-dione: 2-(2-methoxyphenoxy) propanedioic acid diethyl ester (2.82 g, 10 mmol) and a solution of 2-amidinopyrimidine benzenesulfonate (2.8 g, 10 mmol) in ethanol (30 mL) were sequentially added to sodium (0.69 g, 30 mmol) dissolved in absolute ethanol (40 mL). The reaction was heated at reflux for about 16 hours, poured onto ice-water, acidified with 3M hydrochloric acid, and concentrated until a precipitate formed. The precipitate was collected by filtration, washed with water and dried to yield 804 mg of desired product as a yellow solid. (25percent yield). 1H NMR (300 MHz, DMSO-d6) δ 3.84 (s, 3H), δ 6.68 (d, J=6.9 Hz, 1H), δ 6.77 (t, J=7.5 Hz, 1H), δ 6.91 (t, J=7.5 Hz, 1H), 7.05 (d, J=6.9 Hz, 1H), 9.05 (d, J=5.1 Hz, 2H), 12.19 (br, 2H); ESI-MS, m/z=313 (M+H+).Step 3 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidine-4,6(1H,5H)-dione: The title compound was made by following the procedure set forth in Example 1, step 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | for 4 h; Reflux | Example 25-(2-methoxyphenyl)-2-(pyrimidin-2-yl)pyrimidin-4,6-(1H,5H)-dione (compound 1) to 4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine (compound 2); Charged 343.70 gm of phosphorous oxychloride followed by 175.0 gm of compound 1. Raised the temperature of reaction mass to reflux. Stirred the reaction mass at reflux for 4.0 hr. Reaction is monitored by HPLC. Cooled the reaction mass gradually to 40-50° C. Quenched the reaction mass slowly into 2.625 lit of water at 5-10° C. Stirred the reaction mass at 5-10° C. for 2.0 hrs. Filtered and washed the wet material thrice with 175.0 ml of water. Unloaded the wet material. Weight wet of Compound 2: 255 gm. Dried the wet material under vacuum at 55-60° C. for 8.0 hrs. Weight of dried compound 2: 182 gm (percent Yield: 93percent; HPLC Purity: >98percent)) |
87% | With phosphorus pentachloride In toluene for 2 h; Reflux | 5- (2-methoxyphenoxy) -1H- [2,2 '] - dipyridyl-4,6-dione (IV) (30 g, 96 mmol)Toluene (400 mL), phosphorus pentachloride (44.0 g, 211.3 mmol) was added and heated to reflux for 2 h. The TLC reaction was complete. (3 mL), and the organic phase was combined, washed with saturated aqueous sodium carbonate solution (100 mL) and saturated brine (100 mL), and the organic phase was washed with water (100 mL) and saturated brine (100 mL) Dried over anhydrous sodium sulfate, and the residue was dried to obtain 29.0 g of the desired product 4,6-dichloro-5- (2-methoxyphenoxy) -2,2 '-bipyridine (V) 87percent. |
86% | at 100℃; for 16 h; | Step 4; 4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine: 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidine-4,6(1H,5H)-dione (804 mg, 2.6 mmol) was added to a mixture of phosphorous oxychloride (8 mL) and 2,4,6-trimethylpyridine (0.312 g, 2.6 mmol). Under continuous stirring, the mixture was heated at about 100° C. for about 16 hours, cooled to ambient temperature, poured onto ice-water, and concentrated in vacuo. The residue was diluted with water, the resulting precipitate was collected by filtration, and dried to give the title compound (776 mg, 86percent). 1H NMR (300 MHz, DMSO-d6) δ 3.84 (s, 3H), 6.87 (t, J=7.5 Hz, 1H), 6.97 (d, J=8.1 Hz, 1H), 7.15 (m, 2H), 7.71 (t, J=4.8 Hz, 1H), 9.07 (d, J=4.8 Hz, 2H); ESI-MS m/z=349 (M+H+).Step 4 4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine: The title compound was made by following the procedure set forth in Example 1, step 4. |
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