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Chemical Structure| 40230-24-8 Chemical Structure| 40230-24-8

Structure of 40230-24-8

Chemical Structure| 40230-24-8

4,6-Diphenylpyrimidin-2-amine

CAS No.: 40230-24-8

4.5 *For Research Use Only !

Cat. No.: A218559 Purity: 97%

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Product Details of [ 40230-24-8 ]

CAS No. :40230-24-8
Formula : C16H13N3
M.W : 247.30
SMILES Code : NC1=NC(C2=CC=CC=C2)=CC(C3=CC=CC=C3)=N1
MDL No. :MFCD00234910
InChI Key :KZUCBEYDRUCBCS-UHFFFAOYSA-N
Pubchem ID :619024

Safety of [ 40230-24-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 40230-24-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 18
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 77.31
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

51.8 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.53
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.18
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.4
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.49
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.28
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.98

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.95
Solubility 0.028 mg/ml ; 0.000113 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.94
Solubility 0.0285 mg/ml ; 0.000115 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-6.33
Solubility 0.000115 mg/ml ; 0.000000465 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.55 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.04

Application In Synthesis of [ 40230-24-8 ]

* 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.

  • Downstream synthetic route of [ 40230-24-8 ]

[ 40230-24-8 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 62961-62-0 ]
  • [ 593-85-1 ]
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  • 2
  • [ 593-85-1 ]
  • [ 120-46-7 ]
  • [ 40230-24-8 ]
  • 3
  • [ 40230-24-8 ]
  • [ 1484-88-4 ]
  • 1-(4,6-diphenyl-2-pyrimidinyl)-2,4,6-triphenylpyridinium perchlorate [ No CAS ]
  • 4
  • [ 40230-24-8 ]
  • [ 108-24-7 ]
  • [ 58413-41-5 ]
  • 5
  • [ 40230-24-8 ]
  • [ 103-72-0 ]
  • [ 102936-62-9 ]
  • 6
  • [ 87286-05-3 ]
  • [ 40230-24-8 ]
  • 7
  • [ 70769-74-3 ]
  • [ 113-00-8 ]
  • [ 40230-24-8 ]
  • 8
  • [ 113-00-8 ]
  • [ 52762-77-3 ]
  • [ 40230-24-8 ]
  • 9
  • [ 50-01-1 ]
  • [ 94-41-7 ]
  • [ 40230-24-8 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In ethanol; for 10h;Reflux; 1,3-Diphenyl propen-2-one (0.01mol) (1) were taken in a 250 mL round bottom flask and dissolved in ethanol (25 mL). To this guanidine chloride (0.01 mol) and ethanolic KOH (5 mL of 40 %) were added. The reaction mixture was refluxed for 10 h. The mixture was then poured into water (ice-cold) and neutralized with dil. HCl. After neutralization, the solid was filtered, washed with excess of water, dried and recrystallized from ethanol from ethanol to give pure product. Spectral data for compound 2: The IR of compound 2 exhibited nu (C=C) stretching = 1537-1494 cm-1, nu(N-H) (1 amine) stretching = 3302 cm-1 and 3475 cm-1, nu (C-N) stretching = 1220.98 cm-1, nu(C-H)(Sp2) stretching = 3180.72 cm-1. 1H NMR (400 MHz, DMSO-d6) delta ppm: 3.43 (s, 3H,-OCH3), 5.1 (s, 2H, -NH2), 7.0 to 8.0 (m, 20H, Ar-H and NH) [9].
  • 13
  • [ 6935-75-7 ]
  • [ 50-01-1 ]
  • [ 40230-24-8 ]
  • 14
  • [ 58544-41-5 ]
  • [ 40230-24-8 ]
  • 15
  • [ 4524-93-0 ]
  • [ 40230-24-8 ]
  • cyclopentanecarboxylic acid-(4,6-diphenyl-pyrimidin-2-yl)-amide [ No CAS ]
  • 16
  • [ 2736-40-5 ]
  • [ 40230-24-8 ]
  • N-(4,6-diphenyl-pyrimidin-2-yl)-2-ethyl-butyramide [ No CAS ]
  • 17
  • [ 40230-24-8 ]
  • [ 79-03-8 ]
  • N-(4,6-diphenyl-pyrimidin-2-yl)-propionamide [ No CAS ]
  • 18
  • [ 40230-24-8 ]
  • [ 3282-30-2 ]
  • N-(4,6-diphenyl-pyrimidin-2-yl)-2,2-dimethyl-propionamide [ No CAS ]
  • 19
  • [ 40230-24-8 ]
  • [ 618-46-2 ]
  • 3-chloro-<i>N</i>-(4,6-diphenyl-pyrimidin-2-yl)-benzamide [ No CAS ]
  • 20
  • [ 40230-24-8 ]
  • [ 4023-34-1 ]
  • cyclopropane carboxylic acid (4,6-diphenyl-pyrimidin-2-yl)-amide [ No CAS ]
  • 21
  • [ 40230-24-8 ]
  • [ 98-88-4 ]
  • N-(4,6-diphenyl-pyrimidin-2-yl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With triethylamine; In 1,4-dioxane;Heating / reflux; To a solution of <strong>[40230-24-8]2-amino-4,6-diphenylpyrimidine</strong> (0.202 mmol, 1 eq. ) in 1,4- dioxane (5mL) was added triethylamine (0.223 mmol, 1.1 eq. ), followed by the appropriate acid chloride (0.304 mmol, 1.5 eq. ). This was then stirred at reflux until no starting material was visible by TLC. Upon completion, the reaction mixture was separated between ethyl acetate (20 mL) and water (20 mL). The aqueous layer was further extracted with ethyl acetate (2 x 20 mL) and the combined organics washed with water and brine. After drying over MgSO¢ and evaporation under reduced pressure, the crude product was purified by column chromatography, eluting with a petroleum ether-ethyl acetate or a dichloromethane-methanol solvent system. Recrystallisation with ethanol or petroleum ether-ethyl acetate gave the corresponding amide in crystalline form. N- (4, 6-Diphenyl-pyrimidin-2-yl) -benzamide (9). Yield 34%; white solid; mp 169-170 C ; 1H NMR 8 (CDC13) : 8.75 (br s, 1H, N-H), 8. 22-8. 17 (m, 4H, ar), 8. 02-7. 98 (m, 2H, ar), 7.90 (s, 1H, pyrimidine-Il), 7.56-7. 52 (m, 9H, ar) ppm. 13C NMR o (CDC13) : 166.1, 136.5, 132.1, 131.0, 128.9, 128.7, 127.2, 108.1 ppm. MS (ES+): 351.50 Da. Anal. (C23Hl7N30) C, H, N.
  • 22
  • [ 40230-24-8 ]
  • [ 874-60-2 ]
  • <i>N</i>-(4,6-diphenyl-pyrimidin-2-yl)-4-methyl-benzamide [ No CAS ]
  • 23
  • [ 40230-24-8 ]
  • [ 122-01-0 ]
  • 4-chloro-<i>N</i>-(4,6-diphenyl-pyrimidin-2-yl)-benzamide [ No CAS ]
  • 24
  • [ 40230-24-8 ]
  • [ 100-07-2 ]
  • <i>N</i>-(4,6-diphenyl-pyrimidin-2-yl)-4-methoxy-benzamide [ No CAS ]
  • 25
  • [ 40230-24-8 ]
  • [ 638-29-9 ]
  • pentanoic acid (4,6-diphenyl-pyrimidin-2-yl)-amide [ No CAS ]
  • 26
  • [ 40230-24-8 ]
  • [ 142-61-0 ]
  • hexanoic acid (4,6-diphenyl-pyrimidin-2-yl)-amide [ No CAS ]
  • 27
  • [ 40230-24-8 ]
  • [ 75-36-5 ]
  • [ 58413-41-5 ]
  • 28
  • [ 40230-24-8 ]
  • [ 79-30-1 ]
  • LUF5737 [ No CAS ]
  • 29
  • [ 40230-24-8 ]
  • [ 141-75-3 ]
  • LUF5735 [ No CAS ]
  • 30
  • [ 40230-24-8 ]
  • [ 3024-72-4 ]
  • 3,4-dichloro-<i>N</i>-(4,6-diphenyl-pyrimidin-2-yl)-benzamide [ No CAS ]
  • 31
  • [ 40230-24-8 ]
  • [ 108-12-3 ]
  • N-(4,6-diphenyl-pyrimidin-2-yl)-3-methylbutyramide [ No CAS ]
  • 32
  • [ 40230-24-8 ]
  • [ 2719-27-9 ]
  • cyclohexanecarboxylic acid-(4,6-diphenyl-pyrimidin-2-yl)-amide [ No CAS ]
 

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