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CAS No. : | 39268-74-1 | MDL No. : | MFCD00223638 |
Formula : | C6H9N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NGWGYIGTWBAKAN-UHFFFAOYSA-N |
M.W : | 139.16 | Pubchem ID : | 45080359 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 37.74 |
TPSA : | 61.03 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) : | -7.01 cm/s |
Log Po/w (iLOGP) : | 1.57 |
Log Po/w (XLOGP3) : | 0.19 |
Log Po/w (WLOGP) : | 0.47 |
Log Po/w (MLOGP) : | -0.52 |
Log Po/w (SILICOS-IT) : | 0.46 |
Consensus Log Po/w : | 0.43 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.13 |
Solubility : | 10.2 mg/ml ; 0.0734 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.03 |
Solubility : | 13.0 mg/ml ; 0.0933 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.8 |
Solubility : | 2.22 mg/ml ; 0.0159 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.79 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | 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 |
---|---|---|
38% | With triethylamine; In ethyl acetate; toluene; at 85℃; for 24.5h;Reflux; | Example 11 Production of 3-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-4-butyl-1-(5-ethoxypyrimidin-2-yl)-6-methylpyridin-2(1H)-one Process 1: Diketene (2.8 mL, 36 mmol) and triethylamine (2 mL, 14 mmol) were added to a toluene (30 mL) solution of <strong>[39268-74-1]2-amino-5-ethoxypyrimidine</strong> (1.4 g, 10 mmol) and stirred for 24 hours at 85 C. The solvent was distilled off and the mixture was added ethyl acetate (10 mL) and heated under reflux for 30 min. After cooling to room temperature, the solution was filtered to obtain 3-acetyl-1-(5-ethoxypyrimidin-2-yl)-4-hydroxy-6-methylpyridin-2(1H)-one (1.10 g, 38%) as a black solid. 1H-NMR (CDCl3) delta: 1.51 (3H, t, J=7 Hz), 1.99 (3H, s), 2.68 (3H, s), 4.22 (2H, t, J=7 Hz), 5.93 (1H, s), 8.52 (2H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 120℃; for 16h;Inert atmosphere; | EXAMPLE 100(RS)-(5-Ethoxy-pyrimidin-2-yl)-(2-fluoro-4-morpholin-2-yl-phenyl)-aminea) (RS)-2-[4-(5-Ethoxy-pyrimidin-2-ylamino)-3-fluoro-phenyl]-morpholine-4-carboxylic acid tert-butyl esterTo a 10 ml glass vial was added (RS)-2-(4-bromo-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (70 mg, Example 96(e)) and <strong>[39268-74-1]5-ethoxy-2-pyrimidinamine</strong> (40.6 mg, CAS 39268-74-1) in dioxane (2 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (13.6 mg), tris(dibenzylideneacetone)dipalladium(0) (7.12 mg) and sodium tert-butoxide (21.0 mg) were then added. The vial was capped and heated at 120 C. for 16 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 50% EtOAc in hexanes) to afford (RS)-2-[4-(5-ethoxy-pyrimidin-2-ylamino)-3-fluoro-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (15 mg, 18%) as a yellow gum. MS (ISP): 441.4 ([M+Na]+), 419.3 ([M+H]+). |
18% | With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 120℃; for 16h;Inert atmosphere; capped vial; | To a 10 ml glass vial was added (RS)-2-(4-bromo-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (70 mg, Example 96(e)) and <strong>[39268-74-1]5-ethoxy-2-pyrimidinamine</strong> (40.6 mg, CAS 39268-74-1) in dioxane (2 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert- butylphosphino-2',4',6'-triisopropylbiphenyl (13.6 mg), tris(dibenzylideneacetone)dipalladium(0) (7.12 mg) and sodium tert-butoxide (21.0 mg) were then added. The vial was capped and heated at 120 C for 16 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 50% EtOAc in hexanes) to afford (RS)-2-[4-(5-ethoxy-pyrimidin-2-ylamino)-3- fluoro-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (15 mg, 18%) as a yellow gum. MS (ISP): 441.4 ([M+Na]+), 419.3 ([M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Process 4: Under argon atmosphere, trimethylaluminum (2 mol/L hexane solution, 0.39 mL, 0.78 mmol) was added to 1,2-dichloroethane (5 mL) solution of <strong>[39268-74-1]2-amino-5-ethoxypyrimidine</strong> (108 mg, 0.78 mmol) at room temperature and stirred for 70 minutes at room temperature. 1,2-dichloroethane solution (2 mL) of methyl (Z)-2-[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-isobutylami de-2-hexenoate (158 mg, 0.39 mmol) was added dropwise thereto at room temperature and refluxed under heating for 3 hours. The reaction mixture was added an aqueous solution of ammonium chloride and chloroform, and filtered through a pad of celite. The organic layer in the filtrate was separated and the aqueous layer was extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residues were subjected to silica gel column chromatography (Flash12M manufactured by Biotage) (chloroform/methanol = 40 : 1) to give 2-{5-[1-(5-ethoxypyrimidin-2-yl)-2-isopropyl-6-oxo-4-propy 1-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitril e (111 mg, 58%) as yellow oil. 1H-NMR(CDCl3, 400 MHz)delta: 0.97(3H, t, J = 7.4 Hz), 1.17(6H, d, J = 6.6 Hz), 1.49(3H, t, J=6.9Hz), 1.66-1.77(2H, m), 2.19-2.32(1H, m), 2.60-2.70(2H, m), 3.93(2H, s), 4.10(2H, q, J = 7.1 Hz), 7.45(1H, td, J = 7.7, 1.1 Hz), 7.60 - 7.67(2H, m), 7.73 - 7.80(3H, m), 8.49 (2H, s), 8.67(1H, d, J = 1.3 Hz). |
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