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CAS No. : | 23945-44-0 | MDL No. : | MFCD00075737 |
Formula : | C5H4N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZXYAAVBXHKCJJB-UHFFFAOYSA-N |
M.W : | 156.10 | Pubchem ID : | 90301 |
Synonyms : |
Uracil 5-carboxylic acid;Isoorotic acid;5-Carboxyuracil
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 33.04 |
TPSA : | 103.54 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) : | -7.08 cm/s |
Log Po/w (iLOGP) : | 0.3 |
Log Po/w (XLOGP3) : | 0.24 |
Log Po/w (WLOGP) : | -0.41 |
Log Po/w (MLOGP) : | -1.14 |
Log Po/w (SILICOS-IT) : | -0.6 |
Consensus Log Po/w : | -0.32 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.3 |
Solubility : | 7.88 mg/ml ; 0.0505 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.97 |
Solubility : | 1.66 mg/ml ; 0.0106 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.14 |
Solubility : | 214.0 mg/ml ; 1.37 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.67 |
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 |
---|---|---|
96.1% | With dihydrogen peroxide; 1-hydroxy-1,2,3-benzotriazine-4(3H)-one In water at 130℃; for 3 h; Autoclave | Add 100 g of thymine and 300 mL of water to the autoclave, and add 35 mL of hydrogen peroxide at a concentration of 30percent.15 g of 1-hydroxy-1,2,3-benzotriazine-4(3H)-one and 35 g of the catalyst prepared in Example 3, replacing the inside of the autoclave with an oxygen atmosphere, and heating to 130 ° C for 3 h.The reaction solution was cooled, filtered, concentrated, and placed in an ice-water mixture to cool.150 g of a white solid was precipitated, the yield was 96.1percent, and the purity was 99.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With N,N-diethylaniline; trichlorophosphate In N,N-dimethyl-formamide at 90℃; for 2.66667 h; Under cold conditions | To 10.0 g (64.06 mmol) of uracil-5-carboxylic acid (Aldrich Chemical Company) partially dissolved in 20 mL of DMF are added, under cold conditions, 59.7 mL (0.64 mol) of phosphorus oxychloride and 10.3 mL (64.7 mmol) of N,N-diethylaniline, and the mixture is then heated at 90° C. for 2 hours 40 minutes. After cooling to room temperature and evaporating off half the excess POCl3, the medium is poured onto ice and then extracted with ether. The ether phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum. 8.1 g (41.97 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid are obtained in a yield of 65percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 0℃; for 16 h; Inert atmosphere; Reflux | Example 9; 7-Amino-8-ethyl-5-oxo-2-[4-(3-pyridin-3-ylmethylureido)phenyl]-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid Methylamide (No. 53)9.1: 2,4-Dihydroxypyrimidine-5-carbonyl Chloride In a 250 ml round-bottomed flask, under a nitrogen atmosphere, 10.0 g (64.0 mmol) of 2,4-dihydroxypyrimidine-5-carboxylic acid are dissolved in 46 ml (500.0 mmol) of POCl3. The temperature of the mixture is reduced to 0° C. by means of an ice bath, and then 47.7 g (230 mmol) of PCl5 are added in small portions. The solution is stirred for 16 h at reflux and the solvents are then evaporated off under reduced pressure. The residue is taken up and triturated in 100 ml of toluene and then filtered. This operation is repeated three times and then the filtrate is evaporated under reduced pressure, so as to give 13.5 g (64.0 mmol) of compound in the form of a yellow oil which is used directly for the next stage. Yield=100percent. |
99% | at 0℃; for 16 h; Reflux | 11.1: 2,4-Dichloropyrimidine-5-carbonyl chloride 2,4-Dihydroxypyrimidine-5-carboxylic acid (10 g, 64 mmol) is dispersed in POCl3 (45 ml) at 0° C. PCl5 (46.6 g, 224 mmol) is carefully added and the mixture is stirred under gentle reflux for 16 h. The slightly yellow solution is evaporated under reduced pressure and the solid is washed with toluene, and the solution is filtered and the filtrate evaporated to give 13.4 g (yd: 99percent) of the compound. 1H NMR, d6-DMSO (300 MHz): 9.13 (s, 1H). |
99% | at 0℃; for 16 h; Reflux | To POC13 (45mL, 0.07 1 mol) in a round bottom flask was added 2,4-dihydroxypyrimidine-5-carboxylic acid(10.00 g, 0.064 mol) portion wise at 0 °C, followed by slow addition of PC15 (46.60 g, 0.229 mol). The reaction mixture was warmed to r.t. and heated to reflux for 16 h. The mixture was concentrated to dryness, slurried with DCM (30 mL), and the solid precipitated was filtered and washed with DCM (2 x 20 mL). The filtrate was evaporated under reduced pressure to afford the title compound (13.900 g, 99percent) as a yellow oil. ‘H NMR (400 MHz, CDC13): ö 9.25 (s, 1H). |
92% | at 115℃; for 12 h; | To a solution of 2,4-dihydroxypyrimidine-5- carboxylic acid (5.0 g, 32.0 mmol) in POCI3 (50 mL) was added PCI5 (23.9 g, 115.2 mmol), and the resulting solution was heated to 115 °C and stirred for 12 h. The solvent was evaporated and the crude residue was diluted with ethyl acetate (100 mL). The solid was filtered and the filtrate was concentrated to give the title compound as brown oil (6.2 g, 92percent). |
4.38 g | for 4.5 h; Reflux | 5.1.32 2,4-Dichloropyrimidine-5-carboxamide (27) To a solution of 2,4-dihydroxypyrimidine-5-carboxylic acid (25) (2.98 g, 19.1 mmol) in POCl3 (7.10 mL, 76.4 mmol) was added PCl5 (13.1 g, 63.0 mmol) and the reaction mixture was refluxed for 4.5 h. After cooling, the reaction mixture was concentrated in vacuo. To the resulting residue, toluene (20 mL) was added and the mixture was concentrated in vacuo again. The residue was dissolved in CH2Cl2 (20 mL) and filtered. The filtrate was concentrated in vacuo to give 2,4-dichloropyrimidine-5-carbonyl chloride (26) as a yellow oil (4.38 g). This compound was used for next reaction without further purification. To a solution of 26 (4.38 g) in CH2Cl2 (5 mL) were added 28percent NH3 aqueous solution (3 mL) and H2O (3 mL) at -10 °C, and the reaction mixture was stirred at -10 °C for 5 min. The organic solvent was removed under reduced pressure and the resulting precipitate was collected by filtration to give the title compound (3.13 g, 16.3 mmol, 85percent from 25) as a pale yellow solid. 1H NMR (DMSO-d6) δ: 8.05 (1H, s), 8.17 (1H, s), 8.90 (1H, s); MS (ESI) m/z: 192 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | at 20 - 115℃; | Procedure 6 - Preparation of 2,4-dichloro-pyrimidine-5-carbonyl chloride :; A mixture of 30,0 g (192 mmol) 5-carboxyuracil, 44,8 ml (480 mmol) phosphorus oxychloride and 132,0 g (634 mmol) phosphorus pentachloride is stirred under <n="214"/>argon for 6 hours at 115 0C. The mixture is then stirred overnight at room temperature. The mixture is filtered and the filter cake then washed with toluene. The filtrate is first concentrated on the rotary evaporator. The residue obtained is then purified by vacuum distillation (80-900C at 0,15 mbar). 26,0 g (123 mmol; corresponding to 64percent of theory) of the product is obtained. |
64% | at 115℃; for 6 h; | A mixture of 30,0 g (192 mmol) 5-carboxyuracil, 44,8 ml (480 mmol) phosphorus oxychloride and 132,0 g (634 mmol) phosphorus pentachloride is stirred under argon for 6 hours at 115° C. The mixture is then stirred overnight at room temperature. The mixture is filtered and the filter cake then washed with toluene. The filtrate is first concentrated on the rotary evaporator. The residue obtained is then purified by vacuum distillation (80-90° C. at 0,15 mbar). 26,0 g (123 mmol; corresponding to 64percent of theory) of the product is obtained. |
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