[ CAS No. 152460-09-8 ]

Name: 152460-09-8|N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine|95%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 152460-09-8 ]

CAS No. :	152460-09-8	MDL No. :	MFCD02179269
Formula :	C₁₆H₁₃N₅O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OJITWRFPRCHSMX-UHFFFAOYSA-N
M.W :	307.31 g/mol	Pubchem ID :	10686149
Synonyms :

Calculated chemistry of [ 152460-09-8 ]

Physicochemical Properties

Num. heavy atoms :	23
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.06
Num. rotatable bonds :	4
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	88.59
TPSA :	96.52 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	2.86
Log Po/w (WLOGP) :	3.5
Log Po/w (MLOGP) :	1.76
Log Po/w (SILICOS-IT) :	0.93
Consensus Log Po/w :	2.25

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.86
Solubility :	0.0422 mg/ml ; 0.000137 mol/l
Class :	Soluble
Log S (Ali) :	-4.55
Solubility :	0.00874 mg/ml ; 0.0000284 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.12
Solubility :	0.000234 mg/ml ; 0.00000076 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.84

Safety of [ 152460-09-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 152460-09-8 ]

* 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.

Upstream synthesis route of [ 152460-09-8 ]
Downstream synthetic route of [ 152460-09-8 ]

[ 152460-09-8 ] Synthesis Path-Upstream 1~1

1
[ 152460-09-8 ]
[ 404844-11-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 249 - 255
[2] Organic Letters, 2012, vol. 14, # 15, p. 3920 - 3923
[3] Tetrahedron Letters, 2012, vol. 53, # 49, p. 6657 - 6661
[4] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495
[5] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 179 - 183[6] Angewandte Chemie, 2015, vol. 127, # 1, p. 181 - 185,5
[7] Patent: US9095622, 2015, B2,

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Yield	Reaction Conditions	Operation in experiment
62%	With sodium hydroxide; In isopropyl alcohol; at 90℃; for 24h;	General procedure: To a solution of <strong>[55314-16-4]3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one</strong> (7a) (1.76 g, 10 mmol) in 2-propanol was added phenyl guanidinium nitrate (5) (1.94 g, 10 mmol) and sodium hydroxide (12 mmol). The reaction mixture was refluxed at 90 C for 24 h and cooled at 0 C. The precipitate was collected by filtration and was washed with water and dried in air. The crude product was recrystallized from propanol to afford the compound 8a as light yellow solid (1.87 g, 62%).
30%	With sodium hydroxide; In isopropyl alcohol; at 80℃; for 24h;	Step 3: 2-methyl-5-nitrophenyl-(4-pyridin-3-yl-pyrimidin-2-yl)-amine: To a suspension of 3-dimethylamino-1-pyridin-3-yl-propenone (1.70 g, 9.6 mmol) and N-(2-methyl-5-nitro-phenyl)-guanidinium nitrate (2.47 g, 9.6 mmol) in 2-propanol (20 mL) was added NaOH (430 mg, 10.75 mmol) and the resulting mixture was refluxed for 24 h. The reaction mixture was cooled to 0 C. and the resulting precipitate was filtered. The solid residue was suspended in water and filtered and then washed with 2-propanol and diethyl ether and dried. 0.87 g (2.83 mmol) of 2-methyl-5-nitrophenyl-(4-pyridin-3-yl-pyrimidin-2-yl)-amine was isolated. (Yield: 30%.)
	With sodium hydroxide; In isopropyl alcohol; for 18h;Heating / reflux;	3-Dimethylamino-1-(3-pyridyl)-2-propen-1-one (25 g, 0.14 mol), 2-methyl-5-nitrophenyl-guanidine nitrate (36 g, 0.14 mol), and sodium hydroxide (6.5 g, 0.163 mol) were dissolved in isopropanol and reacted under reflux for 18 hours. The reaction solution was cooled to 0 C., filtered, washed with isopropanol and methanol, and dried to give N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine (20 g). Rf=0.6 (Methylene chloride:Methanol=9:1). 1H-NMR(DMSO-d6)=2.43(s, 3H), 7.50-7.60(m, 2H), 7.89-7.93(m, 1H), 8.47-8.50 (m, 1H), 8.62-8.64(m, 1H), 8.71-8.74(m, 1H), 8.78-8.81(m, 1H), 9.27-9.33(m, 2H).

20 g	With sodium hydroxide; In isopropyl alcohol; for 18h;Reflux;	Dimethylamino-1-(3-pyridyl)-2-propen-1-one 4 (25g, 0.14mol), 2-methyl-5-nitrophenyl-guanidine nitrate 2 (36g, 0.14mol), and sodium hydroxide powder (6.5g, 0.163mol) were dissolved in isopropanol and reacted under reflux for 18h. The reaction solution was cooled to 0C, filtered, washed with isopropanol and MeOH, and dried to give N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine 5 (20g). Rf=0.6 (DCM/MeOH, 9:1). NMR was in agreement with the reference.
	With sodium hydroxide; In isopropyl alcohol; for 12h;Heating / reflux;	Experimental Preparation of intermediates; Synthesis of 6-methyl-Nl-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-l,3-diamine 5; To 2-amino-4-nitro toluene 1 (0.033 mol) in n-butanol (29 mL) is added nitric acid (2.1 g, <n="28"/>65% in water) followed by cyanamide solution in water (2 mL, 0.047 mmol). The resulting mixture is heated at reflux for 25 h. After cooling to 0 0C, filtration and washing with 1 : 1 = ethanol : diethyl ether (30 mL), 2-methyl-5-nitrophenyl guanidine nitrate 2 is obtained. To 2-methyl-5-nitrophenyl guanidine 2 (0.0074 mol) in isopropanol (15 mL) is added 3 (0.0074 mol) and sodium hydroxide flakes (0.008 mol). The resulting mixture is heated at reflux for 12 h. After cooling to 0 0C, the product is collected by filtration and washed with isopropanol (6 mL) and methanol (3 mL) to afford 4. 1H NMR (400MHz, Cl6-DMSO) delta 9.31 (s, IH), 9.24 (s, IH), 8.78 (m, IH), 8.70 (m, IH), 8.61 (m, IH), 8.47 (m, IH), 7.88 (m, IH), 7.55 (m, 3H), 2.39 (s, 3H). MS (m/z) (M+l)+: 278.2

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In butan-1-ol; for 38h;Heating / reflux;	A 250 ml reactor, equipped with a mechanical stirrer and a reflux condenser, was charged with 2-chloro-4-(3-pyridyl)-pyrimidine (0.5 g, 2.6 mmol), 2-amino-4-nitrotoluene (0.5 g, 3.2 mmol), n-butanol (15 ml) and concentrated HCl (5 drops) and the mixture was refluxed for 38 hours. Then, the mixture was cooled, and 6 N NaOH was added to pH 8. The solvent was evaporated under reduced pressure and water (20 ml) was added to the residue, followed by extraction with dichloromethane (2×20 ml). The combined organic phase was concentrated to dryness to give the crude N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-pyrimidine-amine, which was purified by column chromatography to yield a product having 80% purity. The residue was re-slurried twice in methanol (2×2 ml) and in water (3 ml) and dried under reduced pressure
290 g	With copper(l) iodide; 2-(dimethylamino)ethyl methacrylate; potassium carbonate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere;	190 g of 2-chloro-4-(pyridin-3-yl)pyridine under a nitrogen atmosphere,167 g of 2-methyl-5-nitroaniline, 47 g of cuprous iodide,Anhydrous potassium carbonate 276gAnd 22 g of dimethylaminoethyl methacrylate added to 1,4-dioxane solution 2000 mLMedium, heating at 100 C, reaction for 20 h, TLC detection,The raw material is completely reacted; first under reduced pressure,Evaporate most of the solvent dioxane, after cooling to room temperature,The reaction mixture was poured into ice water and a large amount of white solid precipitated.Filtration, a small amount of n-hexane rinse, vacuum dry to pureN-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine 290 g.

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate;	Step 20.3 A suspension of 143.0 g (0.46 mol) of <strong>[152460-09-8]N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine</strong> in 7.15 liters of ethyl acetate is stirred with 14.3 g of palladium on active carbon (10% Pd) under a hydrogen atmosphere at normal pressure for 6.5 hours. The suspension is filtered and the filtrate is concentrated in a rotary evaporator. The crude product is recrystallized from methylene chloride, yielding N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine; m.p. 138-140, Rf =0.36 (methylene chloride:methanol=9:1).
	In ethyl acetate;	A suspension of <strong>[152460-09-8]N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine</strong> (1.5 g, 4.6 mmol) and palladium on active carbon (150 mg, 10%) in ethyl acetate (100 ml) was hydrogenated under a hydrogen atmosphere for 2 hours. The reaction was filtered and the filtrate was concentrated to give N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine for future use without further purification.

[ CAS No. 152460-09-8 ]

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