2587-02-2

Basic information

• Product Name: 4-Amino-2,6-dichloropyridine
• Synonyms: 2,6-Dichloropyridine-4-amine;4-Amino-2,6-dichloropyridine, 98+%;4-Amino-2,6-dichloropyridine ,97%;(4-AMino-2,6-dichloropyridine)4-AMino-2,6-dichloropyridine;NSC 136573;4- aMino-2,6- twochlorine pyridine;4-AMino-2,6-dichloropyridine 97%;4-AMino-2,6-dichloropyridine, 97.5%
• CAS NO: 2587-02-2
• Molecular Formula: C₅H₄Cl₂N₂
• Molecular Weight: 163
• EINECS: -0
• Product Categories: Pyridine;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Amines;Aromatics;Heterocycles;Building Blocks;C5;C5 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Heterocycle-Pyridine series
• Mol File: 2587-02-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 169-173 °C(lit.)
• Boiling Point: 336.7 °C at 760 mmHg
• Flash Point: 157.4 °C
• Appearance: White to buff/Powder
• Density: 1.497 g/cm³
• Vapor Pressure: 0.00011mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 0.49±0.50(Predicted)
• BRN: 114351
• CAS DataBase Reference: 4-Amino-2,6-dichloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-2,6-dichloropyridine(2587-02-2)
• EPA Substance Registry System: 4-Amino-2,6-dichloropyridine(2587-02-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2587-02-2(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C5H4Cl2N2/c6-4-1-3(8)2-5(7)9-4/h1-2H,(H2,8,9)/p+1

Synthetic route

2,6-dichloro-4-nitro-pyridine (25194-01-8) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
With hydrogenchloride; iron In ethanol; water at 95℃; for 16h;	95.1%
With hydrogenchloride; water; iron In ethanol at 95℃; for 16h;	95.1%
With ammonium hydroxide In tetrahydrofuran at 95℃; for 4h;	82%

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) + trifluoroacetic acid (76-05-1) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Stage #1: 2,6-dichloropyridine-4-carboxylic acid; trifluoroacetic acid With sodium azide; oxalyl dichloride In dichloromethane Curtius Rearrangement; Heating / reflux; Stage #2: With potassium carbonate In methanol	78%

2,4,6-trichloropyridine (16063-69-7) → 2,6-dichloro-[4]pyridylamine (2587-02-2) + 2-amino-4,6-dichloropyridine (116632-24-7)

Conditions	Yield
With ammonium hydroxide In water at 130℃; for 4h;	A n/a B 67%
With ammonium hydroxide at 160℃;

2,6-dichloropyridine (2402-78-0) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Stage #1: 2,6-dichloropyridine With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex Inert atmosphere; Stage #2: With C10H17NO In tetrahydrofuran; toluene at -25℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere;	64%
Multi-step reaction with 3 steps 1: CF3COOH; aq. H2O2 / 6.5 h / Heating 2: HNO3; H2SO4 / 160 °C 3: AcOH; Fe / Heating View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate; trifluoroacetic acid; dihydrogen peroxide / chloroform; water 2: nitric acid; sulfuric acid 3: hydrogenchloride / ethanol; water View Scheme

2,6-dichloropyridine (2402-78-0) → 2,6-dichloro-[4]pyridylamine (2587-02-2) + 2,2',6,6'-tetrachloro-4,4'-bipyridine (53344-76-6)

Conditions	Yield
With potassium permanganate; ammonia; potassium amide 1.) DME, -70 deg C, 2.) DME, -70 deg C; Yield given. Multistep reaction. Yields of byproduct given;

2.6-dichloro-4-ethoxycarbonylamino-pyridine → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
With potassium hydroxide

2,6-Dichloro-N-(2,2,2-trifluoro-acetyl)-isonicotinamide → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
With potassium carbonate In methanol for 8h;	5.93 g

2,6-dichloroisonicotinoyl chloride (42521-08-4) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Stage #1: 2,6-dichloroisonicotinoyl chloride With sodium azide In water; acetone Stage #2: With trifluoroacetic acid In benzene for 16h; Heating; Stage #3: With potassium carbonate In methanol for 8h;	5.93 g
Multi-step reaction with 3 steps 1: sodium azide / water; acetone / 0.03 h / 25 °C 2: trifluoroacetic acid / benzene / 21 h / 90 °C 3: potassium carbonate / methanol / 7.5 h / 25 °C View Scheme

2,6-dichloropyridine N-oxide (2587-00-0) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating View Scheme
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid 2: hydrogenchloride / ethanol; water View Scheme
Multi-step reaction with 2 steps 1.1: nitric acid; sulfuric acid / water / 1 h / 148 - 156 °C 1.2: pH 6 2.1: hydrogenchloride; iron / ethanol; water / 16 h / 95 °C View Scheme
Multi-step reaction with 2 steps 1.1: nitric acid; sulfuric acid / 1 h / 148 - 156 °C 1.2: 20 °C / pH 6 2.1: hydrogenchloride; water; iron / ethanol / 16 h / 95 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; potassium nitrate / 7 h / 20 - 100 °C 2: acetic acid; iron / 3 h / 45 °C View Scheme

methyl 2,6-dichloroisonicotinate (42521-09-5) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: lithium hydroxide monohydrate / tetrahydrofuran; water / 0.33 h / 25 °C 2: oxalyl dichloride / dichloromethane; tetrahydrofuran / 4 h / 25 °C 3: sodium azide / water; acetone / 0.03 h / 25 °C 4: trifluoroacetic acid / benzene / 21 h / 90 °C 5: potassium carbonate / methanol / 7.5 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 50 - 55 °C 2: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 3: sodium hydroxide / toluene; water / 60 - 70 °C / pH 7 - 8 4: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 50 - 55 °C 2: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 3: sodium hydroxide / toluene; water / 90 - 100 °C / pH 7 - 8 4: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme

citrazinic acid (99-11-6) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: trichlorophosphate / 24 h / 130 °C 2: lithium hydroxide monohydrate / tetrahydrofuran; water / 0.33 h / 25 °C 3: oxalyl dichloride / dichloromethane; tetrahydrofuran / 4 h / 25 °C 4: sodium azide / water; acetone / 0.03 h / 25 °C 5: trifluoroacetic acid / benzene / 21 h / 90 °C 6: potassium carbonate / methanol / 7.5 h / 25 °C View Scheme
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 40 - 105 °C 1.2: 20 - 60 °C 2.1: hydrazine hydrate / ethanol / 50 - 55 °C 3.1: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 4.1: sodium hydroxide / toluene; water / 60 - 70 °C / pH 7 - 8 5.1: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 40 - 105 °C 1.2: 20 - 60 °C 2.1: hydrazine hydrate / ethanol / 50 - 55 °C 3.1: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 4.1: sodium hydroxide / toluene; water / 90 - 100 °C / pH 7 - 8 5.1: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 40 - 105 °C 2.1: thionyl chloride / dichloromethane / 0 - 45 °C 2.2: 0 - 10 °C 3.1: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 4.1: sodium hydroxide / toluene; water / 60 - 70 °C / pH 7 - 8 5.1: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 40 - 105 °C 2.1: thionyl chloride / dichloromethane / 0 - 45 °C 2.2: 0 - 10 °C 3.1: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 4.1: sodium hydroxide / toluene; water / 90 - 100 °C / pH 7 - 8 5.1: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: oxalyl dichloride / dichloromethane; tetrahydrofuran / 4 h / 25 °C 2: sodium azide / water; acetone / 0.03 h / 25 °C 3: trifluoroacetic acid / benzene / 21 h / 90 °C 4: potassium carbonate / methanol / 7.5 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1.1: thionyl chloride / dichloromethane / 0 - 45 °C 1.2: 0 - 10 °C 2.1: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 3.1: sodium hydroxide / toluene; water / 60 - 70 °C / pH 7 - 8 4.1: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme
Multi-step reaction with 4 steps 1.1: thionyl chloride / dichloromethane / 0 - 45 °C 1.2: 0 - 10 °C 2.1: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 3.1: sodium hydroxide / toluene; water / 90 - 100 °C / pH 7 - 8 4.1: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme

2,6-dichloropyridine-4-carbonylazide (81001-09-4) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid / benzene / 21 h / 90 °C 2: potassium carbonate / methanol / 7.5 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / toluene; water / 60 - 70 °C / pH 7 - 8 2: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / toluene; water / 90 - 100 °C / pH 7 - 8 2: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme

2,6-dichloro-4-isocyanatopyridine (159178-03-7) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Stage #1: 2,6-dichloro-4-isocyanatopyridine With potassium carbonate In methanol at 25℃; for 7.5h; Stage #2: With water	4.11 g
With hydrogenchloride In water; toluene at 40 - 45℃;

2,6-dichloro-4-nitropyridine-1-oxide (2587-01-1) + 2,6-dichloro-4-nitro-pyridine (25194-01-8) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
With iron; acetic acid at 45℃; for 3h;	1.3 g

tert-butyl (2,6-dichloropyridin-4-yl)carbamate (501907-61-5) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
With hydrogenchloride In water; toluene at 40 - 45℃;

2,6-dichloro-isonicotinic acid hydrazide (57803-51-7) → 2,6-dichloro-[4]pyridylamine (2587-02-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 2: sodium hydroxide / toluene; water / 60 - 70 °C / pH 7 - 8 3: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride; sodium nitrite / toluene; water / 0 - 10 °C 2: sodium hydroxide / toluene; water / 90 - 100 °C / pH 7 - 8 3: hydrogenchloride / toluene; water / 40 - 45 °C View Scheme

2,6-dichloro-[4]pyridylamine (2587-02-2) → 2,6-dichloro-N-nitro-4-pyridinamine (2587-03-3)

Conditions	Yield
With sulfuric acid; nitric acid at 0℃; for 2h;	100%
With sulfuric acid; nitric acid In water at -5 - 10℃; for 2.66667h;	100%
With sulfuric acid; nitric acid at -5℃;	100%

2,6-dichloro-[4]pyridylamine (2587-02-2) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(2,6-dichloro-pyridin-4-yl)-acetamide (1352830-49-9)

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl acetamide at 100℃; for 7h;	97%

2,6-dichloro-[4]pyridylamine (2587-02-2) + pent-4-enoyl chloride (39716-58-0) → C10H10Cl2N2O

Conditions	Yield
With N-ethyl-N,N-diisopropylamine	97%

2,6-dichloro-[4]pyridylamine (2587-02-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl N-tert-butoxycarbonyl-N-(2,6-dichloro-4-pyridyl)carbamate (1044148-88-0)

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran at 25℃; for 16h;	96%
Stage #1: 2,6-dichloro-[4]pyridylamine With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 16h;	96%

2,6-dichloro-[4]pyridylamine (2587-02-2) → 2,6-dichloro-3-nitropyridin-4-amine (2897-43-0)

Conditions	Yield
Stage #1: 2,6-dichloro-[4]pyridylamine With sulfuric acid at -5℃; Stage #2: With nitric acid In water at 0 - 80℃; Stage #3: With ammonia In water pH=~ 4; Cooling with acetone-dry ice;	94%
With sulfuric acid; nitric acid at 0 - 20℃; for 1h; Inert atmosphere;	80%
With sulfuric acid; nitric acid at 0 - 80℃; for 2h;	74%

2,6-dichloro-[4]pyridylamine (2587-02-2) + benzaldehyde (100-52-7) → C12H10Cl2N2 (868665-68-3)

Conditions	Yield
Stage #1: 2,6-dichloro-[4]pyridylamine; benzaldehyde In toluene for 12h; Heating / reflux; Stage #2: With sodium tetrahydroborate In ethanol at 50 - 75℃; for 2h;	94%

2,6-dichloro-[4]pyridylamine (2587-02-2) + 5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione (15568-85-1) → 5-[[(2,6-dichloropyridin-4-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione (863785-65-3)

Conditions	Yield
In isopropyl alcohol at 70℃; for 4h;	94%
In isopropyl alcohol Heating;	92%
In isopropyl alcohol at 110℃; for 3h;
In isopropyl alcohol at 20 - 75℃; for 0.75h;

2,6-dichloro-[4]pyridylamine (2587-02-2) + trityl chloride (76-83-5) → C24H18Cl2N2 (1352830-73-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 16h;	93.8%

2,6-dichloro-[4]pyridylamine (2587-02-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2,6-dichloropyridin-4-yl)carbamate (501907-61-5)

Conditions	Yield
With dmap In dichloromethane at 20℃;	93%
With sodium hexamethyldisilazane In tetrahydrofuran at 29℃; for 3h;
With sodium hexamethyldisilazane In tetrahydrofuran
With dmap In tetrahydrofuran at 60 - 70℃; for 23h;	2.04 g

2,6-dichloro-[4]pyridylamine (2587-02-2) + sodium methylate (124-41-4) → 2-chloro-6-methoxy-pyridin-4-ylamine (1008304-85-5)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In methanol at 100℃; for 7h; Reagent/catalyst; Solvent; Autoclave;	91.9%
In 1-methyl-pyrrolidin-2-one at 140℃;	74%

2,6-dichloro-[4]pyridylamine (2587-02-2) + phenylboronic acid (98-80-6) → 4-amino-2,6-diphenylpyridine (52816-93-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 5h; Inert atmosphere;	89%

2,6-dichloro-[4]pyridylamine (2587-02-2) + sodium ethanolate (141-52-6) → 2-chloro-6-ethoxy-pyridin-4-amine (904311-14-4)

Conditions	Yield
In ethanol at 150℃; for 6h;	88%
In ethanol at 150℃; for 6h; Sealed tube;	88%
In ethanol at 150℃; for 2h;

2,6-dichloro-[4]pyridylamine (2587-02-2) + 2-Ethoxycarbonyl-7-methoxybenzofuran-4-carboxylic acid → ethyl 4-[(3,5-dichloro-pyridin-4-yl)carbamoyl]-7-methoxybenzofuran-2-carboxylate (222297-34-9)

Conditions	Yield
With hydrogenchloride; thionyl chloride In tetrahydrofuran; dichloromethane	88%

morpholine (110-91-8) + 2,6-dichloro-[4]pyridylamine (2587-02-2) → 2-chloro-6-(morpholin-4-yl)-pyridin-4-ylamine (878809-77-9)

Conditions	Yield
In 1,4-dioxane at 150℃;	87.8%
at 150℃; for 4h; Sealed tube;	85%
at 150℃; for 4h; Sealed tube;	85%

methanol (67-56-1) + 2,6-dichloro-[4]pyridylamine (2587-02-2) + sodium methylate (124-41-4) → 2-chloro-6-methoxy-pyridin-4-ylamine (1008304-85-5)

Conditions	Yield
at 130 - 160℃; Inert atmosphere;	87%

2,6-dichloro-[4]pyridylamine (2587-02-2) + (N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-methyl-1,2,3-thiadiazole-5-formamide) → N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-N'-(2,6-dichloropyridin-4-yl)-4-methyl-1,2,3-thiadiazole-5-formamidine

Conditions	Yield
With thionyl chloride; dicyclohexyl-carbodiimide In sulfolane for 8h; Inert atmosphere; Autoclave; Reflux;	86.4%

2,6-dichloro-[4]pyridylamine (2587-02-2) + octahydropyrrolo[1,2-a]pyrazine (5654-83-1) → 2-chloro-6-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)pyridin-4-amine

Conditions	Yield
In sulfolane at 150℃;	85%

2,6-dichloro-[4]pyridylamine (2587-02-2) + 1-((4,5-dihydro-1H-imidazol-1-yl)sulfonyl)pyrrolidine-3-carbonyl chloride → N-(2,6-dichloropyridin-4-yl)-1-((4,5-dihydro-1H-imidazol-1-yl)sulfonyl)pyrrolidine-3-carboxamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	85%

methanol (67-56-1) + 2,6-dichloro-[4]pyridylamine (2587-02-2) → 2-chloro-6-methoxy-pyridin-4-ylamine (1008304-85-5)

Conditions	Yield
With sodium methylate for 72h; Reflux;	81.2%
at 150℃; for 0.5h; Microwave irradiation;	79%
With sodium In methanol at 150℃; for 0.5h; Microwave irradiation;	79%

2,6-dichloro-[4]pyridylamine (2587-02-2) + 2,5-dimethoxytetrahydrofuran (34160-24-2) → 2,6-dichloro-4-(1H-pyrrol-1-yl)pyridine (805229-07-6)

Conditions	Yield
With acetic acid at 90℃; for 2h;	80%

2,6-dichloro-[4]pyridylamine (2587-02-2) + bromobenzene (108-86-1) → 2,6-dichloro-N,N-diphenylpyridin-4-amine (929033-63-6)

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux;	78%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux;	15g

2,6-dichloro-[4]pyridylamine (2587-02-2) + 4-tolylacetic acid (622-47-9) → N-(2,6-dichloropyridin-4-yl)-2-(p-tolyl)acetamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h;	77%

piperidine (110-89-4) + 2,6-dichloro-[4]pyridylamine (2587-02-2) → 2-chloro-6-(piperidin-1-yl)pyridin-4-amine

Conditions	Yield
at 140℃; for 4h;	77%

2,6-dichloro-[4]pyridylamine (2587-02-2) + C15H11ClN2O → 1-benzyl-3-(2,6-dichloropyridin-4-yl)-3,4-dihydro-4-iminoquinazolin-2(1H)-one

Conditions	Yield
Stage #1: 2,6-dichloro-[4]pyridylamine With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: C15H11ClN2O In tetrahydrofuran at -78 - 20℃; for 2h;	76%

2,6-dichloro-[4]pyridylamine (2587-02-2) + 4-chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene (1380809-63-1) → (2,6-dichloropyridin-4-yl)-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophen-4-ylamine (1380808-60-5)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 16h;	73%

2,6-dichloro-[4]pyridylamine (2587-02-2) + 3-bromo-1-(4-methoxybenzyl)-1H-[1,2,4]triazole → (2,6-dichloropyridin-4-yl)-[1-(4-methoxybenzyl)-1H-[1,2,4]triazol-3-yl]amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos In toluene at 20 - 110℃; Inert atmosphere;	72%

2,6-dichloro-[4]pyridylamine (2587-02-2) + pivaloyl chloride (3282-30-2) → N-(2,6-dichloro-4-pyridinyl)-2,2-dimethylpropanamide (1345456-45-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 13h;	70%
With triethylamine In dichloromethane Cooling with ice;
With triethylamine In dichloromethane Cooling with ice;	11.59 g

2-(morpholin-4-yl)ethanol (622-40-2) + 2,6-dichloro-[4]pyridylamine (2587-02-2) + bis(trichloromethyl) carbonate (32315-10-9) → 2-(morpholin-4-yl)ethyl (2,6-dichloropyridin-4-yl)carbamate (1432740-81-2)

Conditions	Yield
Stage #1: 2,6-dichloro-[4]pyridylamine; bis(trichloromethyl) carbonate With triethylamine In benzene for 5h; Reflux; Stage #2: 2-(morpholin-4-yl)ethanol In benzene at 20℃;	70%

Upstream product

• 2402-78-0 2,6-dichloropyridine 
• 5398-44-7 2,6-dichloropyridine-4-carboxylic acid 
• 76-05-1 trifluoroacetic acid 
• 57803-51-7 2,6-dichloro-isonicotinic acid hydrazide 
• 501907-61-5 tert-butyl (2,6-dichloropyridin-4-yl)carbamate 
• 2587-01-1 2,6-dichloro-4-nitropyridine-1-oxide 
• 25194-01-8 4-nitro-2,6-dichloro-pyridine 
• 159178-03-7 2,6-dichloro-4-isocyanatopyridine 
• 81001-09-4 2,6-dichloropyridine-4-carbonylazide 
• 99-11-6 citrazinic acid 
• 42521-09-5 methyl 2,6-dichloroisonicotinate 
• 2587-00-0 2,6-dichloropyridine N-oxide 
• 42521-08-4 2,6-dichloroisonicotinoyl chloride 
• 16063-69-7 2,4,6-trichloropyridine 

Downstream Products

• 894803-87-3 4-amino-6-ethoxypyridine-2-carboxylic acid methyl ester 
• 904312-12-5 4-amino-6-ethoxy-5-iodo-N-[4-(methylsulfonyl)benzyl]pyridine-2-carboxamide 
• 916673-06-8 4-amino-2-ethoxy-6-(4-methanesulfonyl-benzylcarbamoyl)-nicotinic acid methyl ester 
• 916673-05-7 4-Amino-6-ethoxy-5-((Z)-2-trimethylsilanyl-but-1-en-3-ynyl)-pyridine-2-carboxylic acid 4-methanesulfonyl-benzylamide 
• 668268-64-2 8-chloro-3-deazaadenine 
• 668268-69-7 3-chloro-3-deazaadenine 
• 668268-68-6 2,6-dichloro-8-oxo-3-deazaadenine 
• 101079-63-4 3,4-diamino-2,6-dichloropyridine 
• 6811-77-4 3-deazaadenine 
• 2589-12-0 4,6-dichloro-1H-imidazo<4,5-c>pyridine 
• 52559-17-8 2-chloro-3-deazaadenine 

Relevant articles and documents

Preparation method of 4-amino-2,6-dichloropyridine

The invention relates to a preparation method of a halogen-substituted pyridylamine compound, particularly to a preparation method of 4-amino-2,6-dichloropyridine, wherein 2,6-dihydroxy isonicotinic acid is used as a raw material and is subjected to chlorination reaction, Curtius rearrangement or further amine protection group removal to obtain the product. The method has the advantages of accessible raw materials, high yield and low impurity content, avoids the use of explosive reagent sodium azide, and can be further applied to industrial production.

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.

Efficient synthesis of 4-amino-2,6-dichloropyridine and its derivatives

A facile synthetic route to an important intermediate 4-amino-2,6-dichloropyridine was developed. Oxidation of 2,6-dichloropyridine as a starting material gave pyridine N-oxide derivative which was subjected to nitration followed by reduction. Subsequent nitration of the product and nucleophilic displacement reaction were carried out to afford fully substituted energetic pyridine derivatives. Most of the synthetic reactions proceeded under mild conditions.