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CAS No. : | 483324-01-2 | MDL No. : | MFCD09743494 |
Formula : | C9H6ClN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MGQROXOMFRGAOY-UHFFFAOYSA-N |
M.W : | 191.62 | Pubchem ID : | 11805543 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 50.27 |
TPSA : | 38.67 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.22 cm/s |
Log Po/w (iLOGP) : | 1.85 |
Log Po/w (XLOGP3) : | 1.76 |
Log Po/w (WLOGP) : | 2.19 |
Log Po/w (MLOGP) : | 0.71 |
Log Po/w (SILICOS-IT) : | 2.61 |
Consensus Log Po/w : | 1.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.75 |
Solubility : | 0.338 mg/ml ; 0.00176 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.19 |
Solubility : | 1.24 mg/ml ; 0.00646 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.42 |
Solubility : | 0.00735 mg/ml ; 0.0000384 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.09 |
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 |
---|---|---|
87% | With ammonium hydroxide In water at 80℃; for 16 h; Sealed tube | Preparation of 4-pyridin-3-yl-pyrimidin-2-ylamine lll-b In a sealed tube, a solution of lll-a (1 .18 g, 6.16 mmol) in 30percent NH4OH (12 mL) was heated at δΟ ' for 16h. After cooling, the precipitate was isolated by filtration, washed with water and dried under vacuum to give the title compound lll-b as a beige solid (925 mg, 87 percent). H NMR (400 MHz, DMSO-d6) δ 9.23 (d, J = 2.1 Hz, 1 H), 8.69 (dd, J = 4.7, 1 .3 Hz, 1 H), 8.43 - 8.38 (m, 1 H), 8.36 (d, J = 5.1 Hz, 1 H), 7.53 (dd, J = 8.0, 4.8 Hz, 1 H), 7.21 (d, J = 5.1 Hz, 1 H), 6.76 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.6% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 4 h; Inert atmosphere; Green chemistry | In a 250 mL three-necked flask,2,4-dichloropyrimidine (5.0 g, 33.56 mmol)Dissolved in 1,4-dioxaneAnd water (4: 1, 50 mL) A solution of 3-boronic acid pyridine (4.95 g, 40.27 mmol),Potassium carbonate (9.28 g, 67.12 mmol)And Pd (dppf) Cl2 (2.45 g, 3.36 mmol);The system was replaced with argon three times,Gradually heated to 90 ° C,Reaction for 4 hours;After the reaction, the system was concentrated under reduced pressure to remove most of the solvent,Ethyl acetate (150 mL)And water (100 mL),Extraction and separation,The aqueous phase was then extracted with ethyl acetate (80 mL)The organic phases were combined,Re-water (80 mL x 2) and saturateWashed with brine (80 mL x 2)Liquid separation,The organic phase was dried over anhydrous sodium sulfate for 3 hours,Filtration and concentration,Crude;The crude product was added petroleum ether (32 mL)And ethyl acetate (6 mL) were stirred for 1 hour,filter,Dried in vacuo to give 4.8 g of 2-chloro-4- (3-pyridyl) pyrimidine,The yield was 74.6percentPurity HPLC was greater than 95percent. |
73% | With sodium carbonate In tetrahydrofuran; water for 16 h; Heating; Reflux; Inert atmosphere | Example 11 Preparation of 2-chloro-4-(pyridin-3-yl)pyrimidine[00106] Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of pyridin-3-ylboronic acid (4.42 g, 36.0 mmol, 1.00 equiv) in THF/H2O (30 mL), a solution of 2,4-dichloropyrimidine (5.40 g, 36.2 mmol, 1.00 equiv) in THF/H2O (30 mL), Na2CO3 (11.5 g, 108 mmol, 3.00 equiv) and PdCl2(PPh3)2 (1.80 g, 2.57 mmol, 0.06 equiv). The resulting solution was heated to reflux for 16 hrs in an oil bath. The reaction mixture was cooled and quenched by the addition of 100 mL of water. The resulting solution was extracted with 5x200 mL of ethyl acetate. The organic layers were combined, washed with 3x200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1: 1). This resulted in 5 g (73percent) of 2-chloro-4-(pyridin-3-yl)pyrimidine as a yellow solid. |
52% | With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane for 14 h; Reflux; Inert atmosphere | General procedure: To a solution of 2,4-dichloro-5-methylpyrimidine (500 mg, 3.1 mmol) and 4-trifluoromethoxylphenylboronic acid (644 mg, 3.1 mmol) in dioxane (15 mL), Pd(PPh3)2Cl2 (215 mg, 0.3 mmol) and 2M Na2CO3 (920 mg, 8.7 mmol) were added. The mixture was stirred at reflux for 14 h under N2 atmosphere. The reaction mixture was cooled to room temperature and filtrated. The filtrate was diluted with H2O (100 mL) and then extracted with EtOAc, and the organic layer was dried over anhydrous Na2SO4, After filtration, the filtrate was evaporation and purified by chromatography (petroleum ether/ EtOAc, 5:1) to give the product as oil (700 mg, 73 percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 1 h; Inert atmosphere Stage #2: at -30 - 0℃; for 1.66667 h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; diethyl ether; hexane; water at 0 - 20℃; for 0.25 h; |
Preparation of 2-chloro-4-pyridin-3-yl-pyrimidine lll-a To a solution of n-butyllithium (2.5 molar in hexane, 13.5 mL, 34 mmol) in anhydrous diethylether (50 mL) under argon at -78 ' was added 3-bromo pyridine (3 mL, 31 mmol). The mixture was stirred for 1 h, then a suspension of 2-chloro pyrimidine (3.6 g, 31 mmol) in anhydrous diethylether (30 mL) was added portionwise over 10 min. The resulting mixture was stirred at -30 °C for 30 min, and then allowed to warm to 0 °C for 1 h, at which point the reaction was successively quenched by addition of water (1 mL) in THF (10 mL) and DDQ (7.6 g, 34 mmol) in THF (25 mL). The resulting brown suspension was stirred at room temperature for 15 min, then cooled to 0 ', and treated with hexane (25 mL) and aqueous NaOH (3N, 25 mL). The mixture was stirred at 0 ' for 5 min, diluted with water (100 mL) and then extracted with ethyl acetate. The combined organic layers were washed with water, dried on MgS04, and concentrated to a minimum volume to afford after filtration lll-a as a pale brown solid (3.14 g, 53 percent). H NMR (400 MHz, DMSO- de) δ 9.35 (dd, J = 2.3, 0.8 Hz, 1 H), 8.90 (d, J = 5.3 Hz, 1 H), 8.79 (dd, J = 4.8, 1 .6 Hz, 1 H), 8.54 (ddd, J = 8.0, 2.3, 1 .7 Hz, 1 H), 8.26 (d, J = 5.3 Hz, 1 H), 7.62 (ddd, J = 8.0, 4.8, 0.8 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | at 70℃; for 6 h; | (2) Feeding: Weigh 2-oxo-4- (3-pyridyl) - pyrimidine and 1.73g thionyl chloride 20.0ml into the reaction flask and catalyst DMF770μL, system reaction 6h after TLC monitoring material point at 70 disappeared, the reaction was completed.Post-treatment: the system to be cooled, the system was poured into 400ml of ice water, adjusted to pH 8 with sodium hydroxide solution, (30ml × 3) and extracted with ethyl acetate, the extract was dried over anhydrous sodium sulfate, suction filtered, the The filtrate was evaporated to dryness to give a pale yellow solid, yield 65percent. |
56% | at 50℃; for 4.5 h; | 2. Preparation of 2-chloro-4-(3-pyridyl)-pyrimidine In a 250 ml two necked flask, equipped with a mechanical stirrer and a condenser, a mixture of 2-oxo-4-(3-pyidyl)-pyrimidine (3 g, 0.017 mol) and POCl3 (18 ml) was stirred at 50° C. for 4.5 hrs. The reaction mixture was poured into cold water (50 ml) and neutralized with 47percent aqueous NaOH solution to pH 8. The solution was extracted with ethyl acetate (2*50 ml). The combined ethyl acetate phase was dried over magnesium sulfate and evaporated to dryness to give 2-chloro-4-(3-pyridyl)-pyrimidine in 56percent yield, having a purity of 97percent. |
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