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CAS No. : | 915070-53-0 | MDL No. : | MFCD06797215 |
Formula : | C7H8BClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JARHIHWQCALALV-UHFFFAOYSA-N |
M.W : | 170.40 | Pubchem ID : | 53216288 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 46.24 |
TPSA : | 40.46 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) : | -6.05 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.82 |
Log Po/w (WLOGP) : | 0.33 |
Log Po/w (MLOGP) : | 1.21 |
Log Po/w (SILICOS-IT) : | 0.34 |
Consensus Log Po/w : | 0.74 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.38 |
Solubility : | 0.709 mg/ml ; 0.00416 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.29 |
Solubility : | 0.875 mg/ml ; 0.00513 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.29 |
Solubility : | 0.882 mg/ml ; 0.00518 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.68 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
67% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; at 85℃; for 16h;Inert atmosphere; | To a stirred solution of <strong>[205672-25-9]5-bromo-2-chloropyrimidin-4-amine</strong> (0.5 g, 2.39 mmol) in THF:H2O (15 ml, 9:1), 2-chloro-3-methylphenyl)boronic acid (2, 0.61 g, 3.58 mol), sodium carbonate (0.71 g, 7.17 mmol) were added. The reaction mixture was degassed with argon for 10 min and Pd(PPh3)4 (0.27 g, 0.24 mmol) was added. The reaction mixture was degassed again with argon and heated at 85 C. with stirring for 16 h. Progress of the reaction was monitored by TLC, which showed consumption of starting material. The reaction mixture was allowed to cool to room temperature and concentrated. The residue was diluted with water (20 mL) and extracted with EtOAc (3*20 mL). The combined organic layer was washed with brine (40 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography [silica gel (100-200 mesh), gradient 6-8% ethyl acetate in hexane] to give 2-chloro-5-(2-chloro-3-methylphenyl)pyrimidin-4-amine (0.4 g, 67%) as a pale yellow solid. MS (ESI+ve): 254.14 1H-NMR (400 MHz; DMSO-d6): delta 7.82 (s, 1H), 7.44-7.46 (d, J=7.20 Hz, 1H), 7.32-7.36 (t, J=7.6 Hz, 1H), 7.18-7.20 (d, J=6.8 Hz, 1H), 2.40 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In 1,4-dioxane; at 85℃; for 12h;Inert atmosphere; | To a stirred solution of <strong>[97329-43-6]1-bromo-2-chloro-3-methylbenzene</strong> (2 g, 9.73 mmol) in 1,4-dioxane (15 mL), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (3.7 g, 14.6 mmol) and potassium acetate (2.86 g, 29.1 mmol) were added. The reaction mixture was degassed with argon for 10 min. Then Pd(PPh3)2Cl2 (1.02 g, 1.45 mmol) was added and heated at 85 C. with stirring for 12 h. The color of the reaction mixture changed from yellow to red and finally to black. Progress of the reaction was monitored by TLC, which showed consumption of starting material. The reaction mixture was cooled to room temperature and filtered through celite, followed by ethyl acetate wash (100 mL). The filtrate was concentrated to dryness under reduced pressure to afford mixtures of product (1.5 g, 60% pure in LCMS) as a red colored oil, which was used directly for the next step. |